Palladium/BINAP(S)-Catalyzed Asymmetric Allylic Amination
- 25 January 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (4) , 633-636
- https://doi.org/10.1021/ol047624k
Abstract
The enantioselective allylic amination of acyclic allylic carbonates catalyzed by a palladium/(S)-BINAP(S) system was investigated. Amination of several substrates proceeded with high ee. Crotyl carbonates show an unusually high regioselectivity for the branched isomer. The use of (S)-TolBINAP(S) and (S)-3,5-xylyl-BINAP(S) as ligands was found to increase the enantioselectivity of the aminations. A P,S binding mode of the BINAP(S) ligand was found in an X-ray crystallographic study. [reaction: see text]Keywords
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