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Synthesis of Polycyclic Tertiary Carbinamines by Samarium Diiodide Mediated Cyclizations of Indolyl Sulfinyl Imines
Author(s) -
Rao Chintada Nageswara,
Lentz Dieter,
Reissig HansUlrich
Publication year - 2015
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/anie.201408324
Subject(s) - enantiopure drug , chemistry , indole test , imine , moiety , samarium , reactivity (psychology) , medicinal chemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , stereochemistry , catalysis , medicine , alternative medicine , pathology
Samarium diiodide mediated cyclizations of N ‐acylated indole derivatives bearing sulfinyl imine moieties afforded polycyclic tertiary carbinamines with moderate to excellent diastereoselectivities. Lithium bromide and water turned out to be the best additives to achieve these transformations in good yields. Using enantiopure sulfinyl imines the outcome strongly depends on the reactivity of the indole moiety. Whereas with unactivated indole derivatives desulfinylation and formation of racemic products was observed, indoles bearing electron‐withdrawing substituents at C‐3 afforded the polycyclic products with intact N ‐sulfinyl groups and with excellent diastereoselectivity, finally allowing the preparation of enantiopure tertiary carbinamines. The mechanisms of these processes are discussed.