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Modular Synthesis of 1,2‐Diamine Derivatives by Palladium‐Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides
Author(s) -
McDonald Richard I.,
Stahl Shan S.
Publication year - 2010
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.200906342
Subject(s) - allylic rearrangement , sulfamide , palladium , oxidative phosphorylation , chemistry , catalysis , tetrahydrofuran , diamine , combinatorial chemistry , organic chemistry , solvent , biochemistry
Allylic sulfamides undergo aerobic oxidative cyclization at room temperature, mediated by a Pd(O 2 CCF 3 ) 2 /DMSO catalyst system in tetrahydrofuran. The cyclic sulfamide products are readily converted into 1,2‐diamines, and substrates derived from chiral allylic amines cyclize with very high diastereoselectivity.