Asymmetric Catalytic Coupling of Organoboranes, Alkynes, and Imines with a Removable (Trialkylsilyloxy)ethyl Group—Direct Access to Enantiomerically Pure Primary Allylic Amines | Zendy

Patel Sejal J. | Zendy; Jamison Timothy F. | Zendy

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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

Author(s) -

Patel Sejal J.,

Jamison Timothy F.

Publication year - 2004

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200460044

Subject(s) - allylic rearrangement , substituent , catalysis , aryl , chemistry , yield (engineering) , primary (astronomy) , coupling (piping) , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , physics , alkyl , astronomy , metallurgy

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.

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