Base catalysed domino and self-domino Michael-Aldol reactions: one-pot synthesis of dispirocyclopentaneoxindoles containing multiple chiral stereocenters

被引：14
|
作者：
Suman, Koorathota [1 ]
Thennarasu, Sathiah [1 ]
机构：
[1] CSIR Cent Leather Res Inst, Organ Chem Lab, Madras 600020, Tamil Nadu, India
来源：
RSC ADVANCES | 2015年 / 5卷 / 30期
关键词：
ASYMMETRIC TOTAL-SYNTHESIS; BAYLIS-HILLMAN CARBONATES; MARINE-DERIVED FUNGUS; DIELS-ALDER REACTION; AZOMETHINE YLIDES; SPIROOXINDOLE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; 3+2 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS;
D O I：
10.1039/c5ra00283d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A one-pot method for the construction of three classes of densely functionalized dispirocyclopentaneoxindoles containing multiple chiral stereocenters is developed. Base promoted self-domino and domino reactions with and without the participation of solvent, alcohol, is accomplished. Piperidine catalyzed self-domino reaction involves the participation of the nucleophilic solvent, alcohol, resulting in complex dispiro compounds containing four and five diastereoisomeric centers. Triethylamine promotes the self-domino reaction between two molecules of 3-phenacylideneoxindoles with added nucleophiles, and not with the solvent nucleophile. Diisopropylethylamine facilitates the domino reaction between 3-phenacylidineoxindole and phenacylacenaphthylenone allowing the construction of novel dispirocyclopentaneoxindoles with high yields and diastereoselectivity. A plausible mechanism is tentatively proposed to account for the diastereoselectivity of the domino Michael-Aldol reaction.
引用
收藏
页码：23291 / 23302
页数：12
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