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Chiral Biscarboline N,N′ ‐Dioxide Derivatives: Highly Enantioselective Addition of Allyltrichlorosilane to Aldehydes
Author(s) -
Bai Bing,
Shen Lan,
Ren Jie,
Zhu Hua Jie
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100592
Subject(s) - chemistry , enantioselective synthesis , catalysis , lewis acids and bases , organic chemistry , aldehyde , base (topology) , medicinal chemistry , mathematical analysis , mathematics
The allylation of aromatic and aliphatic aldehydes with allyltrichlorosilanes has been catalyzed with a new Lewis base organocatalyst, 1,1′‐biscarboline N,N′ ‐dioxide with high enantioselectivities of up to 99% for 4‐methoxybenzaldehyde and 97% ee for cycloformaldehyde, respectively. In total, 13 heteroaryl and aliphatic aldehydes were tested.