Enantiocontrolled synthesis of 2,2,6-trisubstituted tetrahydropyrans using η3-pyranylmolybdenum π-complexes as organometallic chirons

ORGN 183

Bo Cheng, bcheng@emory.edu and Lanny S. Liebeskind, chemLL1@emory.edu. Department of Chemistry, Emory University, 1515 Dickey Dr NE, Atlanta, GA 30322
η3-Pyranylmolybdenum π-complexes as organometallic chirons have been demonstrated as excellent scaffolds in the enantiocontrolled synthesis of highly functionalized heterocycles. Recently, a novel methodology has been developed in the stereoselective synthesis of 2,2,6-trisubstituted tetrahydropyans. Through sequential Mukaiyama-Aldol reaction, semipinacol rearrangement, “1,5-Michael-Type” reaction and demetallation, the 5-oxo-TpMo(CO)2(pyranyl) complex can be transformed to various 2,2,6-trisubstituted tetrahydropyrans with complete control of stereochemistry.
 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006