Diastereoselective and Enantioselective Alleno-aldol Reaction of Allenoates with Isatins to Synthesis of Carbinol Allenoates Catalyzed by Gold

被引：88
|
作者：
Wang, Gang [1 ]
Liu, Xiaohua [1 ]
Chen, Yushuang [1 ]
Yang, Jian [1 ]
Li, Jun [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ,2 ]
机构：
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
来源：
ACS CATALYSIS | 2016年 / 6卷 / 04期
基金：
中国国家自然科学基金;
关键词：
aldol reaction; allenes; asymmetric catalysis; carbinol allenoates; gold catalysis; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; BETA-KETOESTERS; ESTERS; KETONES; DERIVATIVES; LIGANDS; PROPARGYL; CHEMISTRY; ALDEHYDES;
D O I：
10.1021/acscatal.6b00294
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A new asymmetric alleno-aldol addition of allenic esters has been developed that allows the formation of trisubstituted and tetrasubstituted carbinol allenoates diastereoselectively and enantioselectively. The nucleophilic additions of achiral and racemic alienates to isatins proceed well in the presence of AuCl3 and chiral N,N'-dioxide under mild reaction conditions. The results reported herein represent the first example of metal complex promoted gamma-selective asymmetric addition of allenic esters to carbonyl compounds.
引用
收藏
页码：2482 / 2486
页数：5
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