Citation: Zhu Mingyu, Deng Weiping. An-PIQ Catalyzed Kinetic Resolution of β-Iodo Morita-Baylis-Hillman Adducts[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2397-2406. doi: 10.6023/cjoc201606039 shu

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

Zhu Mingyu ,
Deng Weiping ^*,,

1.
Shanghai Key Laboratory of Functional Materials Chemistry & School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Corresponding author: Deng Weiping, weiping_deng@ecust.edu.cn
Received Date: 26 June 2016
Revised Date: 24 July 2016

Fund Project: National Natural Science Foundation of China 21372074

Figures(2)

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.
- β-iodo MBH adducts,
- nucleophilic catalysis,
- enantioselectivity,
- kinetic resolution
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