Stereoselective Mannich Reaction of N-(tert-Butylsulfinyl) imines with 3-Fluorooxindoles and Fluoroacetamides

被引：32

作者：

Chen, Xiangyu ^{[1
]}

Li, Ya ^{[1
]}

Zhao, Jianbo ^{[1
]}

Zheng, Buquan ^{[1
]}

Lu, Qi ^{[1
]}

Ren, Xinfeng ^{[1
]}

机构：

[1] Shanghai Univ Engn Sci, Dept Chem & Chem Engn, 333 Longteng Rd, Shanghai 201620, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 17期

基金：

上海市自然科学基金;

关键词：

fluorine; asymmetric synthesis; amides; amines; chiral auxiliaries; CATALYTIC ENANTIOSELECTIVE FLUORINATION; QUATERNARY STEREOGENIC CENTERS; CHIRAL BETA-FLUOROAMINES; ASYMMETRIC-SYNTHESIS; HETEROCYCLIC CHEMISTRY; AMINES; APPLICATION; ALLYLIC ALKYLATION; CARBOXYLATE ESTERS; EFFICIENT ACCESS; AROMATIC KETONES;

D O I：

10.1002/adsc.201700353

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A diastereoselective Mannich reaction has been developed for the construction of stereogenic C-F units by the reaction of alpha-fluorosubstituted amides, including highly activated 3fluoro- oxindoles, and simple linear fluoroacetamides with N-tert-butylsulfinylimines. This method provides a concise route to a variety of structurally diverse alpha-fluoro-beta-amino amides containing stereogenic fluorinated carbon centers. This protocol has the benefit of using readily accessible starting materials and is operationally simple. The Mannich reactions of cyclic and linear a-fluoro-substituted amides resulted in different stereochemical outcomes, suggesting that these substrates reacted via closed and open transition states, respectively.

引用

页码：3057 / 3062

页数：6

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