A 1,3,2-Diazaphospholene-Catalyzed Reductive Claisen Rearrangement

1,3,2-Diazaphospholenes (DAPs) are an emerging class of organic hydrides. In this work, we exploited them as efficient catalysts for very mild reductive Claisen rearrangements. The method is tolerant towards a wide variety of functional groups and operates at ambient temperature. Besides being enantiospecific for substrates with existing stereogenic centers, the diastereoselectivity can be switched by varying solvents and DAP catalysts. The reaction kinetics show direct rearrangements of O-bound phospholene enolates and provide a proof-of-principle for catalytic enantioselective reactions.


Published in:
Angewandte Chemie-International Edition, 58, 26, 8893-8897
Year:
Jun 24 2019
Publisher:
Weinheim, WILEY-V C H VERLAG GMBH
ISSN:
1433-7851
1521-3773
Keywords:
Laboratories:




 Record created 2019-07-25, last modified 2019-07-28


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