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Zinc Homologation–Elimination Reaction of α‐Sulfinyl Carbanions as a New Route to Olefins
Author(s) -
Abramovitch Adi,
Marek Ilan
Publication year - 2008
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.200800529
Subject(s) - carbanion , transmetalation , chemistry , zinc , tandem , reductive elimination , elimination reaction , derivative (finance) , medicinal chemistry , organic chemistry , catalysis , materials science , financial economics , economics , composite material
α‐Lithiosulfinyl carbanions react either intermolecularly, after transmetalation into an organocopper derivative in an S N 2‐type process, with zinc carbenoids, or intramolecularly by higher‐order zincates through a tandem zinc homologation–β‐elimination reaction into the corresponding alkenes. α,α‐ and α,β‐Disubstituted alkenes can also be produced through these two methodologies.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)