Issue 24, 2016
From the journal:

Organic & Biomolecular Chemistry

Catalytic asymmetric formal γ-allylation of deconjugated butenolides†

Amit K. Simlandya  and  Santanu Mukherjee*a  

* Corresponding authors

a Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
E-mail: sm@orgchem.iisc.ernet.in
Fax: +91-80-2360-0529
Tel: +91-80-2293-2850

Abstract

A formal γ-allylation of deconjugated butenolides is reported based on a two-step sequence consisting of a catalytic diastereo- and enantioselective vinylogous nucleophilic addition to vinyl sulfones and Julia–Kocienski olefination. This highly modular approach delivers densely functionalized butenolides containing a quaternary stereogenic centre in excellent yield with high enantioselectivity.

Graphical abstract: Catalytic asymmetric formal γ-allylation of deconjugated butenolides

  • This article is part of the themed collection: New Talent
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Article information

DOI
https://doi.org/10.1039/C5OB02362A
Article type
Paper
Submitted
17 Nov 2015
Accepted
30 Nov 2015
First published
30 Nov 2015

Org. Biomol. Chem., 2016,14, 5659-5664

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Catalytic asymmetric formal γ-allylation of deconjugated butenolides

A. K. Simlandy and S. Mukherjee, Org. Biomol. Chem., 2016, 14, 5659 DOI: 10.1039/C5OB02362A

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