Diastereodivergent Synthesis of Enantiomerically Pure Homoallylic Amine Derivatives Containing Quaternary Carbon Stereocenters | Zendy

Kolodney Goren | Zendy; Sklute Genia | Zendy; Perrone Sylvie | Zendy; Knochel Paul | Zendy; Marek Ilan | Zendy

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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.

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