4.7 Article

Noncovalent Interactions in the Oxazaborolidine-Catalyzed Enantioselective Mukaiyama Aldol

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 15, 页码 10054-10061

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01039

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  1. EPSRC [EP/R513155/1, EP/W003724/1]
  2. University of Bath

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A new reaction model relying on different interactions between the nucleophile, electrophile, and catalyst has been proposed to explain the selectivity in the oxazaborolidine-catalyzed Mukaiyama aldol reaction, as the current models based on hydrogen bonding alone are insufficient.
Current models for oxazaborolidine-catalyzed transition-state structures are determined by C-H center dot center dot center dot O-B and C-H center dot center dot center dot O=S formyl hydrogen bonding between the electrophile and catalyst. However, selectivity in the oxazaborolidine-catalyzed Mukaiyama aldol cannot be fully rationalized using these models. Combined density functional theory and noncovalent interaction analyses reveal a new reaction model relying on C-H center dot center dot center dot O, C-H center dot center dot center dot pi, and pi-pi interactions between the nucleophile, electrophile, and catalyst to induce selectivity.

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