a simple organocatalytic enantioselective cyclopropanation of α,β-unsaturated aldehydes

2007 Cyclopropane derivatives Q 0021 A Simple Organocatalytic Enantioselective Cyclopropanation of α,β-Unsaturated Aldehydes. — The cyclopropanation of α,β-unsaturated aldehydes (I) with bromoma- lonate (II) proceeds efficiently in the presence of O-silyl diarylprolinol derivatives (DPPL or DXPL) to furnish the corresponding formylcyclopropanes (III) in high dia- stereo- and enantioselectivity (up to 99% e.e.). The cyclopropanation of hexadienal (IV) is regiospecific. — (RIOS, R.; SUNDEN, H.; VESELY, J.; ZHAO, G.-L.; DZIEDZIC, P.; CORDOVA*, A.; Adv. Synth. Catal. 349 (2007) 7, 1028-1032; Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.; Eng.) — Mischke 37- 066

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Page 1: A Simple Organocatalytic Enantioselective Cyclopropanation of α,β-Unsaturated Aldehydes

2007

Cyclopropane derivativesQ 0021 A Simple Organocatalytic Enantioselective Cyclopropanation of α,β-Unsaturated

Aldehydes. — The cyclopropanation of α ,β-unsaturated aldehydes (I) with bromoma-lonate (II) proceeds efficiently in the presence of O-silyl diarylprolinol derivatives(DPPL or DXPL) to furnish the corresponding formylcyclopropanes (III) in high dia-stereo- and enantioselectivity (up to 99% e.e.). The cyclopropanation of hexadienal (IV) is regiospecific. — (RIOS, R.; SUNDEN, H.; VESELY, J.; ZHAO, G.-L.; DZIEDZIC, P.; CORDOVA*, A.; Adv. Synth. Catal. 349 (2007) 7, 1028-1032; Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.; Eng.) — Mischke

37- 066

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