Jump to main content
Jump to site search

Issue 38, 2012
Previous Article Next Article

Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

Author affiliations

Abstract

The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The “size” of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products.

Graphical abstract: Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 20 Jun 2012, accepted on 01 Aug 2012 and first published on 02 Aug 2012


Article type: Paper
DOI: 10.1039/C2OB26185E
Citation: Org. Biomol. Chem., 2012,10, 7721-7729
  •   Request permissions

    Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

    N. Schläger and A. Kirschning, Org. Biomol. Chem., 2012, 10, 7721
    DOI: 10.1039/C2OB26185E

Search articles by author

Spotlight

Advertisements