Premium
Diastereodivergent Synthesis of Enantiomerically Pure Homoallylic Amine Derivatives Containing Quaternary Carbon Stereocenters
Author(s) -
Kolodney Goren,
Sklute Genia,
Perrone Sylvie,
Knochel Paul,
Marek Ilan
Publication year - 2007
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.200702981
Subject(s) - stereocenter , alkyne , chemistry , amine gas treating , enantiomer , copper , organic chemistry , iodide , quaternary carbon , enantioselective synthesis , catalysis
Freedom of choice : Both enantiomers of free homoallylic amines with two stereogenic centers (including a quaternary center) can be prepared at will from vinyl copper intermediates derived from either a vinyl iodide or an alkyne (see examples; the sulfinyl group is cleaved readily under mild acidic conditions). In this one‐pot strategy, zinc homologation of the vinyl copper species is followed by treatment with a sulfinylimine derivative.