Domino Imino-Aldol-Aza-Michael Reaction: One-Pot Diastereo- and Enantioselective Synthesis of Piperidines

被引：33
|
作者：
Ghorai, Manas K. [1 ]
Halder, Sandipan [1 ]
Das, Raj Kumar [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 21期
关键词：
RING-CLOSING METATHESIS; AMINO BETA-KETOESTERS; DIELS-ALDER REACTION; FUNCTIONALIZED TRANS-2,6-DISUBSTITUTED PIPERIDINES; CATALYTIC ASYMMETRIC-SYNTHESIS; 2,6-DISUBSTITUTED PIPERIDINES; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED PIPERIDINES; EFFICIENT SYNTHESIS; ALKALOID SYNTHESIS;
D O I：
10.1021/jo101680f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Addition of alpha-arylmethylidene- or alpha-alkylidene-beta-keto ester enolate to N-activated aldimines via the imino aldol pathway followed by intramolecular aza-Michael reaction in a domino fashion has been developed, and a highly diastereoselective route to substituted piperidines is reported. Enantiopure piperidines are synthesized from chiral sulfinyl imines. Formation and the observed stereoselectivity of the products have been rationalized by mechanistic and computational studies.
引用
收藏
页码：7061 / 7072
页数：12
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