Catalytic asymmetric torgov cyclization: A concise total synthesis of (+)-estrone

Sébastien Prévost; Nathalie Dupré; Markus Leutzsch; Qinggang Wang; Vijay Wakchaure; Benjamin List

doi:10.1002/anie.201404909

Catalytic asymmetric torgov cyclization: A concise total synthesis of (+)-estrone

Sébastien Prévost
, Nathalie Dupré
, Markus Leutzsch
, Qinggang Wang
, Vijay Wakchaure
, Benjamin List

Max-Planck-Institut für Kohlenforschung

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	8770-8773
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	33
DOIs	https://doi.org/10.1002/anie.201404909
Publication status	Published - 11 Aug 2014
Externally published	Yes

Keywords

disulfonimides
estrone
organocatalysis
torgov cyclization
total synthesis

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10.1002/anie.201404909

Cite this

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abstract = "An asymmetric Torgov cyclization, catalyzed by a novel, highly Br{\o}nsted 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.",

keywords = "disulfonimides, estrone, organocatalysis, torgov cyclization, total synthesis",

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T2 - A concise total synthesis of (+)-estrone

AU - Prévost, Sébastien

AU - Dupré, Nathalie

AU - Leutzsch, Markus

AU - Wang, Qinggang

AU - Wakchaure, Vijay

AU - List, Benjamin

PY - 2014/8/11

Y1 - 2014/8/11

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AB - 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.

KW - disulfonimides

KW - estrone

KW - organocatalysis

KW - torgov cyclization

KW - total synthesis

U2 - 10.1002/anie.201404909

DO - 10.1002/anie.201404909

M3 - Article

C2 - 25080299

AN - SCOPUS:84905857890

SN - 1433-7851

VL - 53

SP - 8770

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 33

ER -

Catalytic asymmetric torgov cyclization: A concise total synthesis of (+)-estrone

Abstract

Keywords

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