Enantioselective Michael Addition of Malonates to Aromatic α,β-Unsaturated Aldehydes Organocatalyzed by (S)-2-[bis(3,4,5-Trifluorophenyl) trimethylsilanyloxymethyl]pyrrolidine

Haiwei      Ye; Yemin      Zheng; Chuanming      Yu; Weihui      Zhong

doi:10.2174/157017811796504927

Abstract

The Michael addition of malonates to aromatic α,β-unsaturated aldehydes was efficiently organocatalyzed by (S)-2-[bis(3,4,5-trifluorophenyl)trimethylsilanyoxymethyl]pyrrolidine, derived from L-proline to afford the corresponding adducts in good yields with good to excellent enantioselectivities.

Keywords: (S)-2-[bis(3,4,5-trifluorophenyl)trimethylsilanyloxymethyl]pyrrolidin, enantioselectivity, Michael addition, organocatalysis, α,β-unsaturated, aldehydes, malonates, L-proline, pyrrolidinemethanol

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Letters in Organic Chemistry

Title: Enantioselective Michael Addition of Malonates to Aromatic α,β-Unsaturated Aldehydes Organocatalyzed by (S)-2-[bis(3,4,5-Trifluorophenyl) trimethylsilanyloxymethyl]pyrrolidine

Volume: 8 Issue: 7

Author(s): Haiwei Ye, Yemin Zheng, Chuanming Yu and Weihui Zhong

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Abstract: The Michael addition of malonates to aromatic α,β-unsaturated aldehydes was efficiently organocatalyzed by (S)-2-[bis(3,4,5-trifluorophenyl)trimethylsilanyoxymethyl]pyrrolidine, derived from L-proline to afford the corresponding adducts in good yields with good to excellent enantioselectivities.

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Ye Haiwei, Zheng Yemin, Yu Chuanming and Zhong Weihui, Enantioselective Michael Addition of Malonates to Aromatic α,β-Unsaturated Aldehydes Organocatalyzed by (S)-2-[bis(3,4,5-Trifluorophenyl) trimethylsilanyloxymethyl]pyrrolidine, Letters in Organic Chemistry 2011; 8 (7) . https://dx.doi.org/10.2174/157017811796504927