Chelate-controlled carbonyl addition reactions. The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride

Authors
Evans, DA Allison, BD Yang, MG
Citation
Da. Evans et al., Chelate-controlled carbonyl addition reactions. The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride, TETRAHEDR L, 40(24), 1999, pp. 4457-4460
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
24
Year of publication
1999
Pages
4457 - 4460
Database
ISI
SICI code
0040-4039(19990611)40:24<4457:CCARTE>2.0.ZU;2-2
Abstract
Highly selective chelation-controlled aidol and allyl nucleophile additions to P-alkoxy aldehydes promoted by dimethylaluminum chloride and methylalum inum dichloride are described. Cationic aluminum chelates are proposed as i ntermediates in these reactions. Evidence is provided to support the claim that chelate organization with Me2AlCl and MeAlCl2 is possible even with be ta-tert-butyldimethyl-silyloxy groups. Stereoselectivity data comparing the chelating potential of Me2AlCl, MeAlCl2, SnCl4, and TiCl4 is provided. (C) 1999 Elsevier Science Ltd. All rights reserved.