Small but effective: Copper hydride-catalyzed synthesis of α-hydroxyallenes

ORGN 585

Norbert Krause, norbert.krause@uni-dortmund.de1, Carl Deutsch1, and Bruce H. Lipshutz, lipshutz@chem.ucsb.edu2. (1) Organic Chemistry II, Dortmund University, Dortmund, Germany, (2) Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106
The copper hydride-catalyzed anti-selective SN2'-reduction of propargyl oxiranes provides an unprecedented, mild and efficient route to α-hydroxyallenes bearing various functional groups (ethers, esters, alcohols, etc.). The highest yields and stereoselectivities are obtained with a copper hydride catalyst (formed in situ from a copper salt and a silane) in the presence of a N-heterocyclic carbene (NHC) ligand. The hydroxy- or dihydroxyallenes formed are highly useful substrates, e.g., for the regio-/chemoselective cycloisomerization to 2,5-dihydrofurans in the presence of a gold precatalyst.

 

Metal-Mediated Reactions and Syntheses
1:00 PM-4:20 PM, Wednesday, March 28, 2007 McCormick Place Lakeside -- Room E350, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007