Catalytic Asymmetric Torgov Cyclization: A Concise Total Synthesis of (+)-Estrone

An asymmetric Torgov cyclization, catalyzed by a novel, highly Brønsted acidic dinitro‐substituted disulfonimide, is described. The reaction delivers the Torgov diene and various analogues with excellent yields and enantioselectivity. This method was applied in a very short synthesis of (+)‐estrone....

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-08, Vol.53 (33), p.8770-8773
Main Authors: Prévost, Sébastien, Dupré, Nathalie, Leutzsch, Markus, Wang, Qinggang, Wakchaure, Vijay, List, Benjamin
Format: Article
Language:English
Subjects:
Acids - chemistry
Asymmetry
Catalysis
Catalysts
Chemical Sciences
Cyclization
Dienes
disulfonimides
estrone
Estrone - chemical synthesis
Estrone - chemistry
Imides - chemistry
Organic chemistry
organocatalysis
Short circuits
Stereoisomerism
Sulfones - chemistry
Synthesis
torgov cyclization
total synthesis
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Summary:An asymmetric Torgov cyclization, catalyzed by a novel, highly Brønsted acidic dinitro‐substituted disulfonimide, is described. The reaction delivers the Torgov diene and various analogues with excellent yields and enantioselectivity. This method was applied in a very short synthesis of (+)‐estrone. A short circuit: An asymmetric Torgov cyclization, catalyzed by a novel, highly Brønsted acidic dinitro‐substituted disulfonimide, is described. The reaction delivers the Torgov diene and various analogues with excellent yields and enantioselectivity. The method was applied in a very short synthesis of (+)‐estrone.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201404909