Format

Send to

Choose Destination
See comment in PubMed Commons below
Chem Rec. 2013 Aug;13(4):362-70. doi: 10.1002/tcr.201300004. Epub 2013 Jul 4.

Enantioselective aldol reactions catalyzed by chiral phosphine oxides.

Author information

1
Priority Organization for Innovation and Excellence, Kumamoto University, Kumamoto 862-0973, Japan.

Abstract

The development of enantioselective aldol reactions catalyzed by chiral phosphine oxides is described. The aldol reactions presented herein do not require the prior preparation of the masked enol ethers from carbonyl compounds as aldol donors. The reactions proceed through a trichlorosilyl enol ether intermediate, formed in situ from carbonyl compounds, which then acts as the aldol donor. Phosphine oxides activate the trichlorosilyl enol ethers to afford the aldol adducts with high stereoselectivities. This procedure was used to realize a directed cross-aldol reaction between ketones and two types of double aldol reactions (a reaction at one/two α position(s) of a carbonyl group) with high diastereo- and enantioselectivities.

KEYWORDS:

aldol reaction; diastereoselectivity; enantioselectivity; organocatalysis; phosphine oxides

PMID:
23828817
DOI:
10.1002/tcr.201300004
[Indexed for MEDLINE]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for Wiley
    Loading ...
    Support Center