Structural studies of boron enolates by X-ray crystallography and DOSY NMR spectroscopy

ORGN 23

Lili Ma, Lili_Ma@Brown.Edu1, Russell Hopson, Russell_Hopson@brown.edu1, and Paul G. Williard, paul_williard@brown.edu2. (1) Chemistry Department, Brown University, Box H, Providence, RI 02912, (2) Department of Chemistry, Brown University, 324 Brook St, Providence, RI 02912
Unlike lithium enolates which exhibit poor diastereoselectivity, boron enolates have excellent control in diastereoselectivity in aldol reactions. Despite the increasing application of boron enolates in complex molecule synthesis, little work is conducted on the physical structures of boron enolates or their reaction intermediates. Based on our long standing interests in the lithium/sodium/potassium/magnium enolate structures, we synthesized and purified the boron enolates. The solid state aggregation and solutions state aggregation of boron enolates were determined by X-ray crystallography and Diffusion Ordered NMR spectroscopy (DOSY).
 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 254 A/B, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007