Carbene-catalyzed atroposelective synthesis of axially chiral styrenes

Jia-Lei Yan, Rakesh Maiti, Shi-Chao Ren, Weiyi Tian (), Tingting Li, Jun Xu, Bivas Mondal, Zhichao Jin and Yonggui Robin Chi ()
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Jia-Lei Yan: Nanyang Technological University
Rakesh Maiti: Nanyang Technological University
Shi-Chao Ren: Nanyang Technological University
Weiyi Tian: Guizhou University of Traditional Chinese Medicine
Tingting Li: Guizhou University, Huaxi District
Jun Xu: Nanyang Technological University
Bivas Mondal: Nanyang Technological University
Zhichao Jin: Guizhou University, Huaxi District
Yonggui Robin Chi: Nanyang Technological University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Axially chiral styrenes bearing a chiral axis between a sterically non-congested acyclic alkene and an aryl ring are difficult to prepare due to low rotational barrier of the axis. Disclosed here is an N-heterocyclic carbene (NHC) catalytic asymmetric solution to this problem. Our reaction involves ynals, sulfinic acids, and phenols as the substrates with an NHC as the catalyst. Key steps involve selective 1,4-addition of sulfinic anion to acetylenic acylazolium intermediate and sequential E-selective protonation to set up the chiral axis. Our reaction affords axially chiral styrenes bearing a chiral axis as the product with up to > 99:1 e.r., > 20:1 E/Z selectivity, and excellent yields. The sulfone and carboxylic ester moieties in our styrene products are common moieties in bioactive molecules and asymmetric catalysis.

Date: 2022
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DOI: 10.1038/s41467-021-27771-x

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