(3R,4R)-2,2,5,5-Tetraphenyltetrahydrofuran-3,4-diol Assisted, L-proline- Catalyzed Michael Addition of Acetone to Nitroalkenes

Xiaoyun      Hu; Zixing      Shan; Chang      Qing

doi:10.2174/157017812802139708

Abstract

(3R,4R)-2,2,5,5-tetraphenyltetrahydrofuran-3,4-diol was employed as additive in the L-proline-catalyzed Michael addition of acetone to nitroalkenes, resulting in upgrading 8-28% ee in enantiomeric purity of the products compared with those without additives.

Keywords: β-nitrostyrene, chiral catalysts, DMSO, ketones, L-proline, michael addition, nitroalkene, acetone, BINOL, enantioselectivity

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Letters in Organic Chemistry

Title:(3R,4R)-2,2,5,5-Tetraphenyltetrahydrofuran-3,4-diol Assisted, L-proline- Catalyzed Michael Addition of Acetone to Nitroalkenes

Volume: 9 Issue: 7

Author(s): Xiaoyun Hu, Zixing Shan and Chang Qing

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Keywords: β-nitrostyrene, chiral catalysts, DMSO, ketones, L-proline, michael addition, nitroalkene, acetone, BINOL, enantioselectivity

Abstract: (3R,4R)-2,2,5,5-tetraphenyltetrahydrofuran-3,4-diol was employed as additive in the L-proline-catalyzed Michael addition of acetone to nitroalkenes, resulting in upgrading 8-28% ee in enantiomeric purity of the products compared with those without additives.

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Hu Xiaoyun, Shan Zixing and Qing Chang, (3R,4R)-2,2,5,5-Tetraphenyltetrahydrofuran-3,4-diol Assisted, L-proline- Catalyzed Michael Addition of Acetone to Nitroalkenes, Letters in Organic Chemistry 2012; 9 (7) . https://dx.doi.org/10.2174/157017812802139708