Microwave-Assisted Organocatalytic Quadruple Domino Reactions of Acetaldehyde and Nitroalkenes

Abstract A microwave-assisted, organocatalytic domino Michael/Henry condensation/Michael/aldol condensation reaction has been developed. Employing acetaldehyde and nitroalkenes as substrates, this quadruple cascade allows an efficient asymmetric synthesis of trisubstituted cyclohexene carbaldehydes...

Full description

Saved in:
Bibliographic Details
Published in:Synthesis (Stuttgart) 2010-02, Vol.2010 (4), p.567-572
Main Authors: Enders, Dieter, Krüll, Ralf, Bettray, Wolfgang
Format: Article
Language:English
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract A microwave-assisted, organocatalytic domino Michael/Henry condensation/Michael/aldol condensation reaction has been developed. Employing acetaldehyde and nitroalkenes as substrates, this quadruple cascade allows an efficient asymmetric synthesis of trisubstituted cyclohexene carbaldehydes in moderate to good yields (25-45%) and high enantioselectivities (ee = 89 to >99%). ESI-MS measurements were carried out to support the proposed complex catalytic cycle.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0029-1217146