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Development of the First Menthane‐Based Chiral Bis(π‐allylpalladium) Catalysis: Asymmetric Allylation of Imines
Author(s) -
Fernandes Rodney A.,
Chaudhari Dipali A.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101588
Subject(s) - chemistry , catalysis , enantioselective synthesis , asymmetric induction , organic chemistry , stereochemistry , medicinal chemistry , combinatorial chemistry
A new ethylidene menthane‐based chiral π‐allylpalladium complex catalyzes the asymmetric allylation of various imines with allyltributylstannane and 1 equiv. of water to give chiral homoallylamines in good yields and enantioselectivities. The reaction was carried out essentially under neutral conditions and displayed a good transfer of chiral information from the menthane skeleton through the formation of a bis(π‐allylpalladium) species. This is the first example of menthane‐based chiral bis(π‐allylpalladium) catalysis.