Chiral phosphoramide-catalyzed, enantioselective, directed cross-aldol reactions of aldehydes

Scott E Denmark, Tommy Bui

Research output: Contribution to journalArticle

Abstract

Catalytic, enantioselective, directed cross-aldol reactions of aldehydes are described. The addition of isobutyraldehyde trichlorosilyl enolate 2 to various aldehydes in the presence of 10 mol % bisphosphoramide 4 provides aldol products in high yields with moderate to good enantioselectivities. The reaction works well with a wide range of aromatic, olefinic, and aliphatic aldehydes. Enantioselectivities are highly dependent on the electronic nature of the aldehyde substituent. Hammett studies reveal that enantioselectivity increases as aldehydes become either more electron rich or more electron poor.

Original languageEnglish (US)
Pages (from-to)5439-5444
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume101
Issue number15
DOIs
StatePublished - Apr 13 2004

ASJC Scopus subject areas

  • General

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