Kinetic Resolution of Sulfinamides via Asymmetric N-Allylic Alkylation

被引：7

作者：

Zheng, Gao-Liang ^{[1
]}

Lu, Chenxi ^{[1
]}

Cheng, Jin-Pei ^{[1
,2
]}

Li, Xin ^{[1
]}

机构：

[1] Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

[2] Tsinghua Univ, Ctr Basic Mol Sci, Dept Chem, Beijing 100084, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 21期

基金：

中国国家自然科学基金;

关键词：

CHIRAL SULFINAMIDES; UMPOLUNG ADDITION; PHOSPHINE OXIDES; SULFOXIDES; ACCESS; OXIDATION; LIGANDS; ACIDS;

D O I：

10.1021/acs.orglett.1c03221

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient kinetic resolution of sulfinamides via an asymmetric N-allylic alkylation reaction was realized using hydroquinine as a catalyst under mild conditions. The kinetic resolution of a range of Morita-Baylis-Hillman adducts and N-aryl tert-butylsulfinamides was highly effective. In addition, the synthetic utility of the protocol was demonstrated by a scaled-up reaction. Density functional theory calculations provide convincing evidence for the interpretation of stereoselection.

引用

页码：8499 / 8504

页数：6

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