Calcium-Catalyzed Asymmetric Synthesis of 3-Tetrasubstituted Oxindoles: Efficient Construction of Adjacent Quaternary and Tertiary Chiral Centers

被引：52

作者：

Shimizu, Shota ^{[1
]}

Tsubogo, Tetsu ^{[1
]}

Xu, Pengyu ^{[1
]}

Kobayashi, Shu ^{[1
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 08期

基金：

日本学术振兴会;

关键词：

STRUCTURE-BASED DESIGN; ENANTIOSELECTIVE CONSTRUCTION; MANNICH REACTIONS; ACID DERIVATIVES; NATURAL-PRODUCTS; GLUTAMIC-ACID; 1,4-ADDITION; POTENT; MICHAEL; SPIROINDOLONES;

D O I：

10.1021/acs.orglett.5b00749

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral Ca-catalyzed asymmetric addition reactions of 3-substituted oxindoles with N-Boc-imines afford 3-tetrasubstituted oxindole derivatives bearing adjacent quaternary and tertiary chiral centers, which are key structures for biological activities. Ubiquitous and nontoxic Ca catalysts (1-10 mol %) work well in this reaction, and high yields (up to >99%) and selectivities (up to >99% ee) of the products with wide substrate scope have been attained. The structures of the chiral Ca catalysts and intermediary Ca enolates are also discussed.

引用

页码：2006 / 2009

页数：4

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