Catalytic Asymmetric Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Linear α-Substituted Monothiomalonates with Isatin N-Boc Ketimines

被引：47

作者：

Liu, Teng ^{[1
]}

Liu, Weiwei ^{[1
]}

Li, Xiaonian ^{[2
]}

Peng, Fangzhi ^{[1
]}

Shao, Zhihui ^{[1
]}

机构：

[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China

[2] Chinese Acad Sci, Kunming Inst Bot, Kunming 650201, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 10期

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; CARBON QUATERNARY STEREOCENTERS; BAYLIS-HILLMAN REACTION; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; BIFUNCTIONAL ORGANOCATALYSTS; BEARING; OXINDOLES; ALKYLATION; CYCLOPROPANATION;

D O I：

10.1021/acs.joc.5b00302

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly diastereo- and enantioselective method for the construction of vicinal tetrasubstituted stereocenters through the first catalytic asymmetric Mannich reaction of linear a-substituted MTMs with isatin N-Boc ketimines has been developed. This protocol provides atom-economic synthesis of less accessible 3-aminooxindoles bearing vicinal tetrasubstituted stereocenters. Notably, it also constitutes the first example of stereoselective synthesis of beta-amino thioesters bearing vicinal tetrasubstituted stereocenters.

引用

页码：4950 / 4956

页数：7