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Atom‐Transfer Tandem Radical Cyclization Reactions Promoted by Lewis Acids
Author(s) -
Yang Dan,
Gu Shen,
Yan YiLong,
Zhao HongWu,
Zhu NianYong
Publication year - 2002
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 - 10.1002/1521-3773(20020816)41:16<3014::aid-anie3014>3.0.co;2-j
Subject(s) - trifluoromethanesulfonate , tandem , pyridine , chemistry , lewis acids and bases , ring (chemistry) , radical cyclization , medicinal chemistry , enantioselective synthesis , catalysis , atom (system on chip) , stereochemistry , organic chemistry , materials science , composite material , computer science , embedded system
Various polycyclic ring skeletons (e.g. 3 ) are formed from unsaturated α ‐bromo β ‐keto esters (e.g. 1 ) in a Lewis acid catalyzed atom‐transfer tandem radical‐cyclization reaction in moderate to good yields and with excellent stereoselectivities. Furthermore, in the presence of chiral complexes such as [Yb(Ph‐pybox)(OTf) 3 ] ( 2 ), the enantioselective cyclization gave up to 84 % ee. OTf = trifluoromethanesulfonate, pybox = 2,6‐bis(2‐oxazolin‐2‐yl)pyridine.