An-PIQ Catalyzed Kinetic Resolution of β-Iodo Morita-Baylis-Hillman Adducts

doi:10.6023/cjoc201606039

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2397-2406.DOI: 10.6023/cjoc201606039 Previous Articles Next Articles

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An-PIQ催化的β-碘代Morita-Baylis-Hillman加合物动力学拆分研究

朱明玉, 邓卫平

华东理工大学药学院上海市功能性材料化学重点实验室上海 200237

收稿日期:2016-06-26 修回日期:2016-07-24 发布日期:2016-08-25
通讯作者: 邓卫平,E-mail:weiping_deng@ecust.edu.cn E-mail:weiping_deng@ecust.edu.cn
基金资助:
国家自然科学基金（No.21372074）资助项目.

An-PIQ Catalyzed Kinetic Resolution of β-Iodo Morita-Baylis-Hillman Adducts

Zhu Mingyu, Deng Weiping

Shanghai Key Laboratory of Functional Materials Chemistry & School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Received:2016-06-26 Revised:2016-07-24 Published:2016-08-25
Supported by:
Project supported by the National Natural Science Foundation of China (No.21372074).

1. An-PIQ Catalyzed Kinetic Resolution of β-Iodo Morita-Baylis-Hillman Adducts.PDF(3376KB)

Abstract

Chiral β-iodo Morita-Baylis-Hillman (MBH) adducts are important versatile synthetic building blocks for many nat-ural products and drug molecules. By using a recently developed acyl transfer catalyst An-PIQ, the kinetic resolutions of a series of β-iodo MBH adducts were investigated, providing the recovered alcohols in good yields with high enantioselectivities (up to 99.9% ee) and good selectivity factors (S up to 165). This method overcomes the issue of low selectivity confronted in the kinetic resolution of aliphatic aldehyde-derived MBH adducts as secondly alcohols, and features mild reaction conditions, broad sub-strate scope, and easy scaling-up to gram scale.

Key words: β-iodo MBH adducts, nucleophilic catalysis, enantioselectivity, kinetic resolution

Cite this article

Zhu Mingyu, Deng Weiping. An-PIQ Catalyzed Kinetic Resolution of β-Iodo Morita-Baylis-Hillman Adducts[J]. Chin. J. Org. Chem., 2016, 36(10): 2397-2406.

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An-PIQ催化的β-碘代Morita-Baylis-Hillman加合物动力学拆分研究

An-PIQ Catalyzed Kinetic Resolution of β-Iodo Morita-Baylis-Hillman Adducts

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