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Diastereoselective Indium‐Promoted Allylation of Chiral N ‐Sulfinyl Imines
Author(s) -
Foubelo Francisco,
Yus Miguel
Publication year - 2014
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.201301068
Subject(s) - chemistry , diastereomer , imine , indium , enantiomer , combinatorial chemistry , enantioselective synthesis , chiral auxiliary , organic chemistry , stereochemistry , catalysis
The indium‐promoted allylation of enantiomerically pure N ‐ tert ‐butylsulfinyl imines has been shown to be a versatile and useful methodology for the preparation of diastereomerically enriched N ‐protected homoallylamines. The preparation of both enantiomeric diastereomers is possible by changing the stereochemistry of the starting imine. Importantly, the deprotection of the sulfinylamines is easily achieved by acid treatment, and, therefore, the corresponding free amines are accessible in an enantioenriched manner. This methodology has been applied to the synthesis of interesting compounds, that is, mostly alkaloids and a wide representation of naturally occurring products.