Experimental mechanistic insight into the BINOL-catalyzed enantioselective conjugate addition of boronates to enones. Issue 23 (3rd June 2015)

• Record Type: Journal Article
• Authors: Nguyen, Thien S.; Yang, Michelle S.; May, Jeremy A.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 23(2015)
• Page Start: 3337
• Page End: 3341
• Publication Date: 2015-06-03
• Subjects: Conjugate addition -- Organocatalysis -- Boronic acids -- Hammett plot -- BINOL; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.166
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The diol-catalyzed enantioselective conjugate addition of boronic acids and boronate esters has seen significant development in the last decade. However, no experimental mechanistic studies related to this transformation have been reported to date. Hammett plot-based analysis of reaction rates has been performed with aryl substitution both at the carbonyl and at the olefin of an enone electrophile. The resulting trends indicate that C–C bond formation is the likely rate limiting step.