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Organocatalytic Enantioselective Aminosulfenylation of α,β‐Unsaturated Aldehydes
Author(s) -
Zhao GuiLing,
Rios Ramon,
Vesely Jan,
Eriksson Lars,
Córdova Armando
Publication year - 2008
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.200802335
Subject(s) - enantioselective synthesis , electrophile , domino , organocatalysis , chemistry , catalysis , organic chemistry , transformation (genetics) , combinatorial chemistry , biochemistry , gene
Domino theory : A simple, highly enantioselective organocatalytic aminosulfenylation of α,β‐unsaturated aldehydes affords orthogonally protected β‐amino‐α‐mercaptoaldehydes in high yields and 93 to >99 %  ee (see scheme, Bn=benzyl). Notably, the catalytic transformation shows that it is possible to efficiently employ all components of an electrophile, which includes a nucleofuge, in organocatalytic domino reactions of enals.

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