Postdoctoral support was provided by the Fonds Québécois de la Recherche sur la Nature et les Technologies (FQRNT, fellowship to C.M.) and Boehringer-Ingelheim (New Investigator Award to T.F.J.). We thank Engelhard-CLAL for a generous donation of [(Ph3P)3RhCl] and the National Institute of General Medical Sciences (GM-063755), the NSF (CAREER CHE-0134704), Amgen, Bristol-Myers Squibb, GlaxoSmithKline, Johnson & Johnson, Merck Research Laboratories, Pfizer, the Sloan Foundation, and MIT for generous financial support. The NSF (CHE-9 809 061 and DBI-9 729 592) and NIH (1S10RR 13886-01) provide partial support for the MIT Department of Chemistry Instrumentation Facility.
Catalytic Reductive Coupling of Epoxides and Aldehydes: Epoxide-Ring Opening Precedes Carbonyl Reduction†
Article first published online: 15 DEC 2004
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 44, Issue 1, pages 129–132, December 17, 2004
How to Cite
Molinaro, C. and Jamison, T. F. (2005), Catalytic Reductive Coupling of Epoxides and Aldehydes: Epoxide-Ring Opening Precedes Carbonyl Reduction. Angew. Chem. Int. Ed., 44: 129–132. doi: 10.1002/anie.200461705
- Issue published online: 15 DEC 2004
- Article first published online: 15 DEC 2004
- Manuscript Received: 18 AUG 2004
- coupling reactions;
Several lines of evidence suggest that reduction of the carbonyl group occurs after epoxide-ring opening in the first examples of catalytic, reductive coupling of epoxides and aldehydes (see scheme). The hydroxyether products are obtained with >95:5 regioselectivity in all cases, independent of the steric and electronic nature of R1 and R2.