A convenient method for the preparation of unsymmetrical bis-aldols by wayof sequential two aldol reactions

Authors
Arai, H Shiina, I Mukaiyama, T
Citation
H. Arai et al., A convenient method for the preparation of unsymmetrical bis-aldols by wayof sequential two aldol reactions, CHEM LETT, (2), 2001, pp. 118-119
Citations number
10
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
03667022 → ACNP
Issue
2
Year of publication
2001
Pages
118 - 119
Database
ISI
SICI code
0366-7022(20010205):2<118:ACMFTP>2.0.ZU;2-5
Abstract
Unsymmetrical alkyl 2-hydroxy-1-(1-hydroxyalkyl)alkyl ketones (bis-aldols) are successfully synthesized by way of sequential two aldol reactions using alpha -bromo ketones and two different aldehydes. In the first reaction, a lpha -bromo-beta -stannyloxy ketones are formed by tin(II) trifluoromethane sulfomate-promoted aldol reaction of alpha -bromo ketones with several alde hydes. Bis-aldols are then formed via the second aldol reaction between ano ther aldehydes and dianionic enolates generated by the reduction of alpha - bromo-beta -metalloxy ketones with titanium(IV) iodide and copper.