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- W2952592017 abstract "Cationic oxazaborolidine 1 affords Diels-Alder adducts of α,β-unsaturated acteylenic ketones with cyclic and acyclic dienes in excellent yields and enantioselectivities. Importantly, dienophiles lacking the typical hydrogen bonding motif as required for other oxazaborolidinium mediated reactions also provide uniformly high levels of asymmetric induction. Subsequently, mechanistic studies of this reaction were undertaken through X-ray crystallographic and computational studies of BF3-acetylene complexes which both indicate a strong preference for syn-coordination geometry of the Lewis acid relative to the alkyne. Thus, we postulate syn-coordination of the acetylene by 1 is operative, which precludes the necessity for hydrogen bonding and maintains close proximity of the reactive sp carbon centers to the chiral environment of the catalyst, ensuring high enantioselectivities." @default.
- W2952592017 created "2019-06-27" @default.
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- W2952592017 date "2010-02-16" @default.
- W2952592017 modified "2023-09-24" @default.
- W2952592017 title "ChemInform Abstract: Cationic-Oxazaborolidine-Catalyzed Enantioselective Diels-Alder Reaction of α,β-Unsaturated Acetylenic Ketones." @default.
- W2952592017 cites W2140501974 @default.
- W2952592017 doi "https://doi.org/10.1002/chin.201007026" @default.
- W2952592017 hasPublicationYear "2010" @default.
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