An Efficient Entry to syn- and anti-Selective Isoindolinones via an Organocatalytic Direct Mannich/Lactamization Sequence

被引：59

作者：

Bisai, Vishnumaya ^{[1
]}

Unhale, Rajshekhar A. ^{[1
]}

Suneja, Arun ^{[1
]}

Dhanasekaran, Sivasankaran ^{[2
]}

Singh, Vinod K. ^{[1
,2
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India

[2] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 09期

关键词：

MANNICH-TYPE REACTIONS; DIRECT ALDOL REACTION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PROLINE; DIAMINES; MICHAEL; CASCADE; AMINES; SCOPE;

D O I：

10.1021/acs.orglett.5b00676

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An organocatalytic direct Mannich-lactamization sequence for the syntheses of pharmacologically important enantioenriched isoindolinones is reported. The method utilizes simple a-amino acids to deliver syn- and anti- selective isoindolinones with remarkably high enantioselectivity (up to >99% ee) in good to excellent yields and diastereomeric ratios. The overall sequence involves one C-C and two C-N bond forming events in one pot starting from inexpensive starting material.

引用

页码：2102 / 2105

页数：4

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