stereoselective synthesis of δ-heteroaryl substituted β-hydroxy-γ,δ-unsaturated α-amino acids

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2007 General R 0010 Stereoselective Synthesis of δ-Heteroaryl Substituted β-Hydroxy-γ,δ-unsaturated α-Amino Acids. — The reaction of β-hetaryl α,β-unsaturated aldehydes (II) with Schoellkopf's reagent proceeds smoothly in the presence of Ti reagent to give the masked β-hydroxy-α-amino acid esters (III)/(IV) which are hydrolyzed under acidic conditions to release the δ-hetaryl-substituted γ,δ-unsaturated β-hydroxy-α-amino acid esters (V). — (CREMONESI, G.; DALLA CROCE, P.; FONTANA, F.; LA ROSA*, C.; Tetrahedron: Asymmetry 17 (2006) 18, 2637-2641; Inst. Chim. Org. A. Marchesini, Fac. Farm., Univ. Milano, I-20133 Milano, Italy; Eng.) — Mischke 10- 112

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Page 1: Stereoselective Synthesis of δ-Heteroaryl Substituted β-Hydroxy-γ,δ-unsaturated α-Amino Acids

2007

GeneralR 0010 Stereoselective Synthesis of δ-Heteroaryl Substituted β-Hydroxy-γ,δ-unsaturated

α-Amino Acids. — The reaction of β-hetaryl α,β-unsaturated aldehydes (II) with Schoellkopf's reagent proceeds smoothly in the presence of Ti reagent to give the masked β-hydroxy-α-amino acid esters (III)/(IV) which are hydrolyzed under acidic conditions to release the δ-hetaryl-substituted γ,δ-unsaturated β-hydroxy-α-amino acid esters (V). — (CREMONESI, G.; DALLA CROCE, P.; FONTANA, F.; LA ROSA*, C.; Tetrahedron: Asymmetry 17 (2006) 18, 2637-2641; Inst. Chim. Org. A. Marchesini, Fac. Farm., Univ. Milano, I-20133 Milano, Italy; Eng.) — Mischke

10- 112