Synlett 2021; 32(20): 2063-2066
DOI: 10.1055/a-1657-5543
letter

Diastereoselective Pd-Catalyzed Decarboxylative Allylation To Construct Quaternary Stereocenters Using Sulfinimine as the ­Directing Group

a   The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin 300071, P. R. of China
,
Chen Li
a   The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin 300071, P. R. of China
,
Xuan Wang
a   The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin 300071, P. R. of China
,
Yilei Huang
a   The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin 300071, P. R. of China
,
Guang Yang
a   The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin 300071, P. R. of China
,
Yunhao Luo
a   The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin 300071, P. R. of China
,
Shuanglin Qin
b   School of Pharmacy, Hubei University of Science and Technology, Xianning 437100, P. R. of China
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (NSFC, 82003186 and 82073691), the Key Research and Development Program of Tianjin City (19YFZCSY00160), the Hubei Science and Technology Program (2020CFB231), the Youth Talent Project of Health Commission of Hubei Province (ZY2021Q026), the Hubei University of Science and Technology (Doctoral Startup Fund Project BK202029).


Abstract

A robust Pd(0)-catalyzed decarboxylation alkylation has been developed to construct quaternary stereocenters through the use of chiral tert-butanesulfinamide as the directing group. This strategy provides a simple and efficient route to the construction of quaternary chiral centers at the α-position of chiral sulfinamides, with high diastereoselectivities and high yields.

Supporting Information



Publication History

Received: 16 August 2021

Accepted after revision: 29 September 2021

Accepted Manuscript online:
29 September 2021

Article published online:
18 October 2021

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