career-in-review keiji maruoka reporter: li chen supervisor: prof. david zhigang wang 2014. 05. 08
Post on 30-Dec-2015
216 Views
Preview:
TRANSCRIPT
Career-in-reviewKeiji Maruoka
Reporter: Li Chen
Supervisor: Prof. David Zhigang Wang
2014. 05. 08
2
Introduction-Keiji Maruoka
EducationB. S. Department of Industrial Chemistry, School of Engineering, Kyoto University 1976Ph.D Department of Chemistry, University of Hawaii 1980 (with Prof. Hisashi Yamamoto)
Professional Appointments1980-1985 Assistant Professor School of Engineering, Nagoya University1985-1989 Lecturer School of Engineering, Nagoya University1990-1995 Associate Professor School of Engineering, Nagoya University1995-2000 Professor Graduate School of Science, Hokkaido University2000-2001 Professor Graduate School of Science, Kyoto University and Hokkaido University2001-present Professor Graduate School of Science, Kyoto University
Prof. Keiji Maruoka
3
Research Career
• Chiral Phase Transfer Catalysts• Alkylations• Enantioselective Synthesis of Amino Acids• Other Alkylations• N-Alkylations• Asymmetric Conjugate Addition• Asymmetric Amination• Aldol Reaction• Epoxidation• Cyanation
• Chiral Organocatalysts• Biaryl-Based Secondary Amine Catalysts• Axially Chiral Dicarboxylic Acid Catalysts
• Bidentate Lewis Acid Catalysts
4
Research Career
• Chiral Phase Transfer Catalysts• Alkylations• Enantioselective Synthesis of Amino Acids• Other Alkylations• N-Alkylations• Asymmetric Conjugate Addition• Asymmetric Amination• Aldol Reaction• Epoxidation• Cyanation
• Chiral Organocatalysts• Biaryl-Based Secondary Amine Catalysts• Axially Chiral Dicarboxylic Acid Catalysts
• Bidentate Lewis Acid Catalysts
5
Chiral Phase Transfer Catalysts
N Br
OH
ArAr
OH
Ar Ar
Ar
Ar(S,S)-2
N
Ar
Ar
Br
(R,R)-1a-f
N
Ar
Ar
Br
R
R
(S)-3
F
F
F
CF3
CF3
F3C
CF3
CF3
F3C
t-Bu
t-Bu
t-Bu
t-Bu
t-Bu
t-Bu
1a:Ar = 1b:Ar = 1c:Ar =
1d:Ar =1e:Ar =1d:Ar =
6
General mechanism
NPh2C
O
OtBuRX NPh2C
O
OtBu
R
cat. Q*X
solvent, MOH*
T. Ooi, K. Maruoka, Angew. Chem. Int. Ed. 2007, 46, 4222.
7
Enantioselective Synthesis of α-Amino Acids
B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1997, 38, 8595.
N CH2 COOtBu
NPh2C
O
OtBuH Ph
NPh2C
O
OtBuH Ph
N
N
HHO
H
H
Cl
N
NHO
H
H
ClH
chiral PTC 4(10 mol%)
chiral PTC 5(10 mol%)
PhCH2Br
50% aq KOH-toluene
20 oC, 18h
Ph2C
Chiral PTC 4 Chiral PTC 5
8
Enantioselective Synthesis of α-Amino Acids
NPh2C
O
OtBuPhCH2Br NPh2C
O
OtBu
CH2Ph
1 mol%(R, R)-1a
toluene/aq KOH
Natural Amino Acids95% yield, 96% ee (R)
N
Ar
Ar
Br
(R, R)-1
Ar =
T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519.
9
Enantioselective Synthesis of α-Amino Acids
N
Br
N
-Np
-Np
Br
Ar1Ar2
Ar2 Ar1
N
BrAr1Ar2
Ar2 Ar1
N
-Np
-Np
Br
atropinversion
homochiral (S, S)-6 homochiral (S, S)-1a
heterochiral (R, S)-1aheterochiral (R, S)-6
diastereomer
(S)-6a: Ar1 = -Np, Ar2 = H
(S)-6b: Ar1 = 3,5-Ph2C6H3, Ar2 = Ph
NPh2C
O
OtBuPhCH2Br NPh2C
O
OtBu
catalyst(1 mol%)
toluene/aq KOH
0 oC H Ph
(S, S)-1a (3 h): 91%, 94% ee(R, S)-1a (60 h): 47%, 11% ee
(S)-6a (18 h): 85%, 87% ee(S)-6b (48 h): 81%, 95% ee
T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. Int. Ed. 2002, 41, 1551.T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Tetrahedron 2006, 62, 11425.
10
Enantioselective Synthesis of α-Amino Acids
M. Kitamura, Y. Arimura, S. Shirakawa, K. Maruoka, Tetrahedron Lett. 2008, 49, 2026.M. Kitamura, S. Shirakawa, Y. Arimura, X. Wang, K. Maruoka, Chem. Asian J. 2008, 3, 1702.
N
Ar
Ar
Br
R
R
(S)-3
COOiPr
COOiPr
Br
Br
Ar B(OH)2 HNR
R
Ar = H, PhX
Y Z
Z
X = OMe, F, Cl, CN, CF3, NO2, Ph, C6F5)
Y = OMe, F, Cl,CN, CF3, NO2
Z = F, Cl, Ph,tBu, CF3
Cl
Cl
Cl
F
F
F
F
F
F
F
FHNR2 = HNMe2, HNBu2, HNHex2, HNDec2, HNiBu2,
HN HNHN
11
Enantioselective Synthesis of α-Amino Acids
M. Kitamura, Y. Arimura, S. Shirakawa, K. Maruoka, Tetrahedron Lett. 2008, 49, 2026.M. Kitamura, S. Shirakawa, Y. Arimura, X. Wang, K. Maruoka, Chem. Asian J. 2008, 3, 1702.
N
Ar
Ar
Br
R
R
(S)-3
COOiPr
COOiPr
Br
Br
Ar B(OH)2 HNR
R
NPh2C
O
OtBuPhCH2Br NPh2C
O
OtBu
(S)-3a(0.01 mol%)
toluene
50 % aq KOH
0 oC, 9 h
H Ph
(R)-8
92%, 98% ee
N
Ar
Ar
Br
Bu
Bu
Simplified Maruoka Catalyst(S)-3a
Ar = 3,4,5-F3-C6H2
12
Asymmetric α,α-Dialkyl-α-Amino Acids Synthesis
T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228.
N
O
OtBu 1 mol% (S,S)-1btoluene/aq CsOH
p-ClPh
Br BrPh
N
O
OtBup-ClPh
Ph
N
O
OtBu 1 mol% (S,S)-1btoluene/aq CsOH
p-ClPh
BrBrPhN
O
OtBup-ClPh
Ph
98% ee
92% ee
N
Ar
Ar
Br
(R, R)-1b
Ar = 3,4,5-F3-C6H2
N
OtBu
Op-ClPh
R1NR4
*
chiral ammonium enolate
13
Other Alkylations
T. Ooi, K. Fukumoto, K. Maruoka, Angew. Chem. Int. Ed. 2006, 45, 3839.
N
O
O
Ph
Ph
O
PhCH2Br
N
O
OPh
O
Ph
Ph
O
NH
Ph
OH
Ph
Ph
(S, S)-7(1 mol%)
25% aq KOH
tBuOMe
0 oC, 7h
dioxane
r.t., 1 h
82%, 92% ee
N
Ar
Ar
BrF3C
F3C
F3C CF3
CF3
CF3
Ar =
(S, S)-7
14
Other Alkylations
T. Hashimoto, K. Sakata, K. Maruoka, Angew. Chem. Int. Ed. 2009, 48, 5014.
COOtBu
Me
Me3Si
PhCH2Br COOtBu
Me3Si
Me Ph
(S)-3a(2 mol%)
KOH
mesitylene
-20 oC, 12h 70%, 86% ee
N
Ar
Ar
Br
Bu
Bu
F
F
F
Ar =
(S)-3a
15
N-Alkylations
S. Shirakawa, K. Liu, K. Maruoka, J. Am. Chem. Soc. 2012, 134, 916.
Me I
Me
HN
O
Me
PhCH2Br Me I
Me
N
O
MePh(S)-3d(2 mol%)
KOH
iPr2O
-20 oC, 24 h
N
Ar
Ar
Br
Hex
Hex
(S)-3d
Ar =
tBu tBu
tBu
tBu
95%, 92% ee
>>
16
Asymmetric Conjugate Addition
R. He, C. Ding, K. Maruoka, Angew. Chem. Int. Ed. 2009, 48, 4559.
N
Ph
O
Boc
O
NO
Boc
Ph O(S)-3c
(3 mol%)
PhCOOK
toluene
-60 oC, 24 h97%, 99% ee
P
Ar
Ar
Br
Bu
Bu
(S)-3c
CF3
CF3
Ar =
17
Asymmetric Conjugate Addition
R. He, S. Shirakawa, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 16620.
NO
Boc
HPh
NO
Boc
DPh
NO
Boc
HPh
(S)-8 (1 mol%)
D2O/toluene
(ratio = 2:1)
5 oC, 2 h 11%88%
N
Ph
O
Boc
NR4*
N
Ph
O
Boc
NO2
NO
Boc
PhNO2
(S)-8(1 mol%)
H2O/toluene
(10:1)
0 oC, 2 h
base-free93%, d.r. 93:7, 90% ee
N
BrCF3
CF3
Ar =
Ph
O
OH
ArAr
OH
Ar Ar
Ph
(S)-8
18
Asymmetric Conjugate Addition
X.Wang,M. Kitamura, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 1038.Q. Lan, X. Wang, K. Maruoka, Tetrahedron Lett. 2007, 48, 4675
COOtBu
Me
NC O
OtBu
OtBuO
NC
Me
COOtBu(S)-9(1 mol%)
Cs2CO3
toluene
-40 oC, 5 h99%, E/Z = 6.7:1
93% ee
O
COOtBu
O
Me
O
COOtBu
O(S)-10(1 mol%)
K2CO3
Et2O
-40 oC, 3 h 98%, E/Z = 1.2:190/85% ee
N
Ar
Ar
Br
X
F3C CF3
CF3
CF3
Ar =
(S)-9 (X = O)(S)-10 (X = NPh)
19
Asymmetric Amination
R. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. Int. Ed. 2008, 47, 9466.R.He, K. Maruoka, Synthesis 2009, 2289.
O
COOtBu
NN
COORROOC
OCOOtBu
N NHCOORROOC
catalyst
K2HPO4
toluene
(S)-3d (3 mol%; -20 oC, 14h);
99%, 91% ee (R = tBu)
(S)-11 (1 mol%; -40 oC, 5h);
99%, 95% ee (R = Et)
P
Ar1
Ar1
Br
Bu
Bu
(S)-3d
Ar1 = 3,5-(CF3)2C6H3
N
Ar2
Ar2
Br
O
(S)-11
Ar2 = 3,5-(3,5-tBu2C6H3)2C6H3
20
Asymmetric Amination
L. Wang, S. Shirakawa, K. Maruoka, Angew. Chem. Int. Ed. 2011, 50, 5327.
NH
OBnBnO NO2Ph
NOBnBnO
PhNO2
(S)-12(0.05 mol%)
H2O/toluene(10:1)
r.t., 8 hbase free
N
BrOH
ArAr
OH
Ar Ar
F3C CF3
CF3
CF3
Ar =
(S)-12
91%, 90% ee
21
Aldol Reaction
T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. Int. Ed. 2002, 41, 4542.
COOtBuNPh2C
PhCHO
COOtBu
Ph OH
NH2
COOtBu
Ph OH
NH2
2 mol% (R,R)-1d
aq NaOHtoluene
1 N HCl
THF
anti-isomer syn-isomer
71% (anti/syn = 12/1)96% ee(anti)
N
Ar
Ar
Br
(R,R)-1
F3C CF3
CF3
CF3
Ar =
22
Epoxidation
T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. Int. Ed. 2002, 41, 4542.T. Ooi, M. Kameda, M. Taniguchi, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 9685.
Ph Ph
O
Ph Ph
OO3 mol% (S,S)-13
13 % NaOCltoluene
99% yield96% ee
N Br
OH
ArAr
OH
Ar Ar
Ar
Ar
(S,S)-13Ar = 3,5-Ph2-C6H3
X-ray structure of 13-PF6 (N, blue; O, red; PF6, green)
23
Cyanation
T. Ooi, Y. Uematsu, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 2548.T. Ooi, Y. Uematsu, J. Fujimoto, K. Fukumoto, K. Maruoka, Tetrahedron Lett. 2007, 48, 1337.
aq KCN
N
H
SO2Ar2
HN
CN
SO2Ar2
Ar2 = 2,4,6-Me3C6H2
(S)-14(1 mol%)
toluene
0 oC, 2 h
NMe
Me
(S)-14
Ar1
Ar1
Ar1
Ar1
CF3Ar1 =
89%, 95% ee
24
Research Career
• Chiral Phase Transfer Catalysts• Alkylations• Enantioselective Synthesis of Amino Acids• Other Alkylations• N-Alkylations• Asymmetric Conjugate Addition• Asymmetric Amination• Aldol Reaction• Epoxidation• Cyanation
• Chiral Organocatalysts• Biaryl-Based Secondary Amine Catalysts• Axially Chiral Dicarboxylic Acid Catalysts
• Bidentate Lewis Acid Catalysts
25
Chiral Secondary Amine Catalysts
T. Kano, K. Maruoka, Chem. Sci. 2013, 4, 907.
Typical secondary amine catalysts derived from proline:
NH
COOH NH
NH
NH
NH
HN NN
N Ar
OHAr
Ph
OTMSPh
Ph
PhPh
L-proline (S)-P1 (S)-P2a (Ar = Ph)(S)-P2b (Ar = 3,5-(CF3)2C6H3
(S)-P3 (S)-P4
NH
COOH
L-proline
NH
R
R'
R'''
R''
R''
R'''
No -Substituent
Mild Basicity and Nucleophilicity
C2-Symmetry (R = R')
Larger Space
Readily Tunable
26
Biaryl-Based Secondary Amine Catalysts
T. Kano, K. Maruoka, Chem. Sci. 2013, 4, 907.
Typical chiral biaryl-based secondary amine catalysts:
NH
NHTf
NH
OH
PhPh
OH
PhPh
NH
OTMS
PhPh
OTMS
PhPh
NH
NHTf
MeO
MeO
NHOMe
OMe
OH
ArAr
OH
ArAr
(S)-15 (S)-16
(S)-19
(S)-17 (S)-18a (Ar = Ph)(S)-18b (Ar = 3,5-F2-C6H3)
27
Aldol Reaction
T. Urushima, Y. Yasui, H. Ishikawa, Y. Hayashi, Org. Lett. 2010, 12, 2966.
Anti-selective aldol reaction of glyoxylate:O
Bn
O
COOEt
O
Bn
COOEt
OH
EtOOCCOOEt
Bn
OH10 mol% (S)-P2a
aq CH3CN
Ph3PCHCOOEt
benzene
92% anti/syn = 20/199% ee (anti)N
H
Ar
OHAr
(S)-P2b Ar = 3,5-(CF3)2C6H3
28
Aldol ReactionAnti-selective aldol reaction of glyoxylate:
O
Bn
O
COOEt
O
Bn
COOEt
OH
EtOOCCOOEt
Bn
OH10 mol% (S)-P2a
aq CH3CN
Ph3PCHCOOEt
benzene
92% anti/syn = 20/199% ee (anti)
Syn-selective aldol reaction of glyoxylate and glyoxamide:
O
Bn
O
COOtBuCOOtBu
O
Bu
OH2 mol% (S)-15
CH3CN
O
Bn
OH
Bu
OH2 mol% (S)-15
CH3CN
O
O
N
O
O
N
O
77% anti/syn = 1/4.796% ee (syn)
82% anti/syn = 1/1797% ee (syn)
NH
NHTf
(S)-15
T. Urushima, Y. Yasui, H. Ishikawa, Y. Hayashi, Org. Lett. 2010, 12, 2966.T. Kano, A. Noishiki, R. Sakamoto, K. Maruoka, Chem. Commun. 2011, 47, 10626.
29
Aldol ReactionAnti-selective aldol reaction of glyoxylate:
O
Bn
O
COOEt
O
Bn
COOEt
OH
EtOOCCOOEt
Bn
OH10 mol% (S)-P2a
aq CH3CN
Ph3PCHCOOEt
benzene
92% anti/syn = 20/199% ee (anti)
T. Urushima, Y. Yasui, H. Ishikawa, Y. Hayashi, Org. Lett. 2010, 12, 2966.T. Kano, A. Noishiki, R. Sakamoto, K. Maruoka, Chem. Commun. 2011, 47, 10626.
Syn-selective aldol reaction of glyoxylate and glyoxamide:O
Bn
O
COOtBuCOOtBu
O
Bu
OH2 mol% (S)-15
CH3CN
77% anti/syn = 1/4.796% ee (syn)
N
Ar
OAr
R
HEtO
O
O
s-trans-enamine
NTfN
OtBuO
O
H
s-cis-enamine
30
Cross-Aldol Reaction
T. Kano, H. Sugimoto, K. Maruoka, J. Am. Chem. Soc. 2011, 133, 18130.
O
iPr
O OH
iPr
OHaminecatalyst
DMF
anti
30 mol% L-proline: 65% anti/syn = 19/1, 96% ee (anti) 5 mol% (S)-16: 90%, anti/syn = 1/20, 96% ee (syn)
Cl
Bn Bn
OH
iPr
OH
Bn
LiAlH4
THF
syn
O
R
O aminecatalyst
Cl
R'
N
R
N
R'
Cl
O
Cl
R'
O
R
OH
Cl
R'R
O OH
RR
O
cross-aldol adduct homo-aldol adduct
more electrophilicacceptor aldehyde
31
Mannich Reaction
J. W. Yang, C. Chandler, M. Stadler, D. Kampen, B. List, Nature, 2008, 452, 453.T. Kano, Y. Yamaguchi, K. Maruoka, Angew. Chem., Int. Ed., 2009, 48, 1838.
NN
N
O
OH
O
R'
Tf
H
O
R'
reactive enamine less nucleophilic enamine
O N
R
O NH20 mol% L-proline
CH3CN
23~58%(TON 1.2~2.9), 96% ee
Boc
R
Boc
O N
R
O NH2 mol% (S)-15
70~92%(TON 35~46), 98% ee
Boc
R
Boc
Suppression of undesired aldol reactions:
32
Conjugate Addition
M. E. Kuehne, P. J. Reider, J. Org. Chem. 1985, 50, 1464.T. Kano, F. Shirozu, K. Tatsumi, Y. Kubota, K. Maruoka, Chem. Sci. 2011, 2, 2311.
O
Bn
OH
Bn
aminecatalyst
Et2OCOOtBu
COOtBu COOtBu
NaBH4
MeOH
COOtBu
10 mol% L-proline: 48%, -6% ee (THF) 3 mol% (S)-20: 83%, 95% ee
Suppression of catalyst consumption:
NH
MeO OMe
HOPh
PhOHPh
Ph
COOtBu
COOtBuO R
N
R
N
COOtBu
tBuOOC
enamineformation
catalystdeactivation
(S)-20
33
α-Hydroxyamination of Aldehydes
G. Zhong, Angew. Chem., Int. Ed. 2003, 42, 4247.T. Kano, M. Ueda, J. Takai, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 6046.
α-Hydroxyamination of aldehydes:
OO
OH5 mol% L-proline
CHCl3
NaBH4
MeOHN
Ph
ONHPh
88%, 97% ee
α-Aminoxylation of aldehydes:
ON
OH10 mol% (S)-17
CHCl3
NaBH4
MeOHN
Ph
OOH
90%, 99% ee
Ph
Plausible transtion state models:
34
Research Career
• Chiral Phase Transfer Catalysts• Alkylations• Enantioselective Synthesis of Amino Acids• Other Alkylations• N-Alkylations• Asymmetric Conjugate Addition• Asymmetric Amination• Aldol Reaction• Epoxidation• Cyanation
• Chiral Organocatalysts• Biaryl-Based Secondary Amine Catalysts• Axially Chiral Dicarboxylic Acid Catalysts
• Bidentate Lewis Acid Catalysts
35
Axially Chiral Dicarboxylic Acid Catalysts
T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 10054.
Mannichi-type addition of diazo compounds:
Ar
COOH
COOH
Ar
Me
Me
t-Bu
Me
Me
MeAr = Ar =
(R)-21a (R)-21b
• Locking the direction of the acidic OH group• Establishing the efficient chiral environment
NBoc
Ar N2
XNHBoc
ArX
N2
(R)-21a (5 mol%)
CH2Cl2, MS4Å
0 oCX = COOtBu or PO(OMe)2 up to 96% ee
36
Axially Chiral Dicarboxylic Acid Catalysts
T. Hashimoto, N. Uchiyama, K. Maruoka, J. Am. Chem. Soc. 2008, 130, 14380.
Trans-selective aziridination:
Ar
COOH
COOH
Ar
Me
Me
t-Bu
Me
Me
MeAr = Ar =
(R)-21a (R)-21b
• Locking the direction of the acidic OH group• Establishing the efficient chiral environment
NBoc
Ar1
N2
Ar1(R)-21b (5 mol%)
toluene, MS4Å
0 oCtrans-selectiveup to 99% ee
O
NH
Ar2
O
NH
Ar2NBoc
37
Axially Chiral Dicarboxylic Acid Catalysts
T. Hashimoto, M. Hirose, K. Maruoka, J. Am. Chem. Soc. 2008, 130, 7556.
Imino-azaenamine reaction:
Ar
COOH
COOH
Ar
Me
Me
t-Bu
Me
Me
MeAr = Ar =
(R)-21a (R)-21b
• Locking the direction of the acidic OH group• Establishing the efficient chiral environment
NBoc
Ar1 N
NHBoc
Ar1 N
Ar2
(R)-21a (5 mol%)
CHCl3, MS4Å
-30 oC84~95% ee
N
H
Ar2
N
38
Research Career
• Chiral Phase Transfer Catalysts• Alkylations• Enantioselective Synthesis of Amino Acids• Other Alkylations• N-Alkylations• Asymmetric Conjugate Addition• Asymmetric Amination• Aldol Reaction• Epoxidation• Cyanation
• Chiral Organocatalysts• Biaryl-Based Secondary Amine Catalysts• Axially Chiral Dicarboxylic Acid Catalysts
• Bidentate Lewis Acid Catalysts
39
Bidentate Lewis Acid Catalysts
H. Hanawa, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 1708.
Bis-Titanium Chiral Lewis Acid Catalyst:
C
O M
A
C
OM
C
OMM
M
B C
C
OMM
D
O
OTi
OiPr
OTi
O
O
iPrO
(S,S)-22
RCHO
SnBu3R
OH5~10 mol% (S,S)-22
CH2Cl2
96~99% ee
OL*Ti TiL*
iPr
iPrO
O
+
-
[ L* = (S)-binaphthoxy ]
OL*Ti TiL*
iPrO
+-
OiPr
HR
1 2
40
Bidentate Lewis Acid Catalysts
H. Hanawa, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 1708.T. Kano, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 11926.
Bis-Titanium Chiral Lewis Acid Catalyst:
C
O M
A
C
OM
C
OMM
M
B C
C
OMM
D
O
OTi
OiPr
OTi
O
O
iPrO
(S,S)-22
RCHO
SnBu3R
OH5~10 mol% (S,S)-22
CH2Cl2
96~99% ee
Bn
N
PhO
OHC
NO
Bn
Ph
HO
10 mol% (S,S)-22
CH2Cl2
NaBH4
EtOH
41
ConclusionBy using "design of catalysts as artificial enzymes" and "environmentally-benign organic synthesis" as two important key-words, the synthetic organic chemistry laboratory focuses on the following topics:1 Design of Chiral Phase Transfer Catalysts for Practical Amino Acid Synthesis2 Design of Chiral Organocatalysts for Practical Asymmetric Synthesis3 Development of Bidentate Lewis Acid Chemistry and Application to Selective Organic Synthesis
42
THANK YOU FOR YOUR ATTENTION!
top related