BINOL Phosphoric Acid-Catalyzed Asymmetric Mannich Reaction of Cyclic N-Acyl Ketimines with Cyclic Enones

被引：18

作者：

Reddy, K. Nagarjuna ^{[1
,3
]}

Rao, M. V. Krishna ^{[1
,3
]}

Sridhar, B. ^{[2
]}

Reddy, B. V. Subba ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, CSIR, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

[3] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2019年 / 14卷 / 17期

关键词：

3-yydroxyisoindolin-1-ones; asymmetric Mannich reaction; cyclic enones; isoindolinones; acyl ketimines; CHIRAL DICARBOXYLIC-ACID; BETA-KETO-ESTERS; BRONSTED ACID; ENANTIOSELECTIVE CONSTRUCTION; SYNTHETIC APPLICATION; IMINES; BOC; ACTIVATION; MOLECULES; DIASTEREO;

D O I：

10.1002/asia.201900556

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantio- and diastereoselective Mannich reaction of cyclic N-acyl ketimines generated in situ from 3-hydroxyisoindolin-1-ones with cyclic enones has been accomplished using a chiral phosphoric acid catalyst to afford the chiral isoindalinone derivatives in high yields with excellent enantioselectivities (upto 97 % ee). This is the first report on the synthesis of chiral isoindolin-1-ones bearing adjacent quaternary and tertiary stereogenic centers.

引用

页码：2958 / 2965

页数：8

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