Amine-stabilized BD3-THF: A new highly efficient deuterium labeling reagent

ORGN 558

Robert C Todd, pgao@sial.com1, Kanth V. B. Josyula, kjosyula@sial.com1, M Mahmun Hossain2, and Peng Gao1. (1) New Product Research & Development, Aldrich Chemical Company, Milwaukee, WI 53209, (2) Department of Chemistry, University of Wisconsin-Milwaukee, 3210 N Cramer Street, Milwaukee, WI WI 53211
Recently we have shown that our newly discovered amine-stabilized borane-tetrahydrofuran (BTHF) complexes are exceedingly valuable reagents in synthetic transformations, such as reduction and hydroboration. We now wish to report on results obtained by extending the scope of our discovery to the amine-stabilized deuterium analog (BD3-THF). Our new amine-stabilized BD3-THF reagent was shown to provide simple access to deuterium labeled compounds of great synthetic importance in high selectivity. Hydroboration studies with this highly reactive BD3-THF adduct and representative olefins such as 1-octene, styrene, 4-bromostyrene, norbornene and allyl chloride were carried out to examine the scope of the complex. Validation of the amine-stabilized BD3-THF reagent was also extended and was shown to be highly efficient in Me-CBS catalyzed reductions of pro-chiral ketones.

 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008