Enantiodivergence by minimal modification of an acyclic chiral secondary aminocatalyst

Jun Dai, Zhuang Wang, Yuhua Deng, Lei Zhu, Fangzhi Peng, Yu Lan () and Zhihui Shao ()
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Jun Dai: Yunnan University
Zhuang Wang: Yunnan University
Yuhua Deng: Yunnan University
Lei Zhu: Chongqing University
Fangzhi Peng: Yunnan University
Yu Lan: Chongqing University
Zhihui Shao: Yunnan University

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: Abstract The development of enantiodivergent catalysis for the preparation of both enantiomers of a chiral compound is of importance in pharmaceutical and bioorganic chemistry. With the design of a class of reactive and stereoselective organocatalysts, acyclic chiral secondary amines, a method for achieving the enantiodivergence is developed simply by changing the secondary N-i-Bu- to N-Me-group within the catalyst architecture while maintaining the same absolute configuration of the catalysts, which modulates the catalyst conformation. This catalyst-controlled enantiodivergent method not only enables challenging asymmetric transformations to occur in an enantiodivergent manner but also features a high level of stereocontrol and broad scope that is demonstrated in eight different reactions (90 examples), all delivering both enantiomers of a range of structurally diverse products including hitherto less accessible, yet important, compounds in good yields with high stereoselectivities.

Date: 2019
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DOI: 10.1038/s41467-019-13183-5

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