Open AccessHow Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones
Author(s) -
Yuhong Lam,
K. N. Houk
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja504714m
Subject(s) - chemistry , cinchona , selectivity , cinchona alkaloids , electrophile , electrophilic fluorination , alkaloid , organic chemistry , ring (chemistry) , ring size , primary (astronomy) , fluorine , catalysis , enantioselective synthesis , physics , astronomy
The origin of selectivity in the α-fluorination of cyclic ketones catalyzed by cinchona alkaloid-derived primary amines is determined with density functional calculations. The chair preference of a seven-membered ring at the fluorine transfer transition state is key in determining the sense and level of enantiofacial selectivity.
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