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Palladium‐Catalyzed Diastereoselective α‐Allylation of Chiral Sulfinimines
Author(s) -
Li Jiangnan,
Jiang Shende,
Procopiou George,
Stockman Robert A.,
Yang Guang
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600615
Subject(s) - chemistry , diastereomer , racemization , palladium , phosphine , catalysis , chiral auxiliary , yield (engineering) , enantioselective synthesis , ligand (biochemistry) , stereochemistry , organic chemistry , combinatorial chemistry , biochemistry , materials science , receptor , metallurgy
The first diastereoselective allylation reaction at the α‐position of ketones by using tert ‐butanesulfinamide as a chiral auxiliary is explored. Excellent yields and high diastereomeric ratios were achieved under palladium catalysis in the presence of a readily available achiral phosphine ligand. The chiral auxiliary was removed in quantitative yield under the optimized conditions without any racemization.