Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

被引：72

作者：

Horwitz, Matthew A. ^{[1
]}

Tanaka, Naoya ^{[2
,3
]}

Yokosaka, Takuya ^{[1
]}

Uraguchi, Daisuke ^{[2
,3
]}

Johnson, Jeffrey S. ^{[1
]}

Ooi, Takashi ^{[2
,3
,4
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

[2] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan

[3] Nagoya Univ, Dept Appl Chem, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648602, Japan

[4] Nagoya Univ, Japan Sci & Technol Agcy JST, CREST, Nagoya, Aichi 4648603, Japan

来源：

CHEMICAL SCIENCE | 2015年 / 6卷 / 11期

关键词：

BROOK REARRANGEMENT REACTION; LOW-VALENT TITANIUM; ALPHA; BETA-UNSATURATED KETONES; STEREOSELECTIVE-SYNTHESIS; ALIPHATIC-ALDEHYDES; CARBONYL-COMPOUNDS; ASYMMETRIC HYDROPHOSPHONYLATION; ALDOL ADDITIONS; AQUEOUS-MEDIA; PINACOL;

D O I：

10.1039/c5sc02170g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A metal-free stereoselective reductive coupling reaction between isatins and aldehydes is reported. The reaction relies on commercial diethyl phosphite (similar to(sic)70 kg(-1)) as the stoichiometric reductant. Base-catalyzed Pudovik addition and phosphonate/phosphate rearrangement achieved polarity inversion on the isatin, and the derived carbanions were trapped by aldehydes with subsequent dialkoxyphosphinyl migration. Chiral iminophosphoranes were used as basic catalysts to achieve high diastereo- and enantioselectivities with excellent yields.

引用

页码：6086 / 6090

页数：5

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