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Catalytic Asymmetric Synthesis of trans ‐Configured β‐Lactones: Cooperation of Lewis Acid and Ion Pair Catalysis
Author(s) -
Kull Thomas,
Cabrera José,
Peters René
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000840
Subject(s) - catalysis , lewis acids and bases , ion , chemistry , lewis acid catalysis , organic chemistry
Abstract The development of the first trans ‐selective catalytic asymmetric [2+2] cyclocondensation of acyl halides with aliphatic aldehydes furnishing 3,4‐disubstituted β‐lactones is described. This work made use of a new strategy within the context of asymmetric dual activation catalysis: it combines the concepts of Lewis acid and organic aprotic ion pair catalysis in a single catalyst system. The methodology could also be applied to aromatic aldehydes and offers broad applicability (29 examples). The utility was further demonstrated by nucleophilic ring‐opening reactions that provide highly enantiomerically enriched anti ‐aldol products.