Issue 42, 2012
From the journal:

Chemical Communications

Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins†

Madhu Sudan Manna,a   Vikas Kumara  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 direct vinylogous Michael reaction of γ-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocenters in excellent yield with perfect diastereoselectivity (>20 : 1 dr) and high enantioselectivity (up to 99 : 1 er).

Graphical abstract: Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins

About
Cited by
Related
Download options Please wait...

Associated articles

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2CC31700A
Article type
Communication
Submitted
07 mar 2012
Accepted
28 mar 2012
First published
28 mar 2012

Chem. Commun., 2012,48, 5193-5195

Permissions

Request permissions

Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins

M. S. Manna, V. Kumar and S. Mukherjee, Chem. Commun., 2012, 48, 5193 DOI: 10.1039/C2CC31700A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements