This work was supported by the National Institute of General Medical Sciences (GM-063755). We also thank the NSF (CAREER CHE-0134704), Merck Research Laboratories, Pfizer, Amgen, Boehringer-Ingelheim, Johnson & Johnson, GlaxoSmithKline, 3M, and MIT for generous financial support. NSF grants CHE-9809061 and DBI-9729592 and NIH grant 1S10RR13886-01 provided partial support for the MIT Department of Chemistry Instrumentation Facility (DCIF). We thank Elizabeth A. Colby and Johann Chan for assistance with the preparation of phosphane ligands.
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Asymmetric Catalytic Coupling of Organoboranes, Alkynes, and Imines with a Removable (Trialkylsilyloxy)ethyl Group—Direct Access to Enantiomerically Pure Primary Allylic Amines†
Article first published online: 20 JUL 2004
DOI: 10.1002/anie.200460044
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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How to Cite
Patel, S. J. and Jamison, T. F. (2004), Asymmetric Catalytic Coupling of Organoboranes, Alkynes, and Imines with a Removable (Trialkylsilyloxy)ethyl Group—Direct Access to Enantiomerically Pure Primary Allylic Amines. Angew. Chem. Int. Ed., 43: 3941–3944. doi: 10.1002/anie.200460044
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Publication History
- Issue published online: 20 JUL 2004
- Article first published online: 20 JUL 2004
- Manuscript Received: 18 MAR 2004
Keywords:
- alkynes;
- allylic amines;
- asymmetric catalysis;
- imines;
- nickel
The aryl substituent on the catalyst is central to the success of the title reaction (see scheme) which affords allylic amines in up to 89 % ee and 91 % yield with a catalyst derived from [Ni(cod)2] and a P-chiral ferrocenyl phosphane (e.g. 1). The coupling products are easily deprotected to enantiomerically enriched, tetrasubstituted primary allylic amines, which can be recrystallized to optical purity.