Noncovalent Interactions in the Oxazaborolidine-Catalyzed Enantioselective Mukaiyama Aldol

Elliot H. E. Farrar, Matthew N. Grayson

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Abstract

Current models for oxazaborolidine-catalyzed transition-state structures are determined by C–H···O–B and C–H···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···O, C–H···π, and π–π interactions between the nucleophile, electrophile, and catalyst to induce selectivity.
Original languageEnglish
Pages (from-to)10054–10061
Number of pages8
JournalThe Journal of Organic Chemistry
Volume87
Issue number15
Early online date18 Jul 2022
DOIs
Publication statusPublished - 5 Aug 2022

Bibliographical note

Funding Information:
This research made use of the Balena High Performance Computing (HPC) Service at the University of Bath. The authors thank the EPSRC, grant numbers EP/R513155/1 (studentship to E.H.E.F.) and EP/W003724/1, and the University of Bath for funding.

ASJC Scopus subject areas

  • Organic Chemistry

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