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.
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Communication
Catalytic Reductive Coupling of Epoxides and Aldehydes: Epoxide-Ring Opening Precedes Carbonyl Reduction†
Article first published online: 15 DEC 2004
DOI: 10.1002/anie.200461705
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
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
- †
Publication History
- Issue published online: 15 DEC 2004
- Article first published online: 15 DEC 2004
- Manuscript Received: 18 AUG 2004
Keywords:
- aldehydes;
- coupling reactions;
- epoxides;
- nickel;
- rhodium
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.