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.
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
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 43, Issue 30, pages 3941–3944, July 26, 2004
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
- Issue published online: 20 JUL 2004
- Article first published online: 20 JUL 2004
- Manuscript Received: 18 MAR 2004
- allylic amines;
- asymmetric catalysis;
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.