Zn(OTf)2 –Cinchona alkaloid-catalyzed asymmetric addition of terminal acetylenes to aldehydes

ORGN 443

Jesper Ekström, jesper@organ.su.se, Alexey B. Zaitsev, and Hans Adolfsson. Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, S-10691 Stockholm, Sweden
Propargylic alcohols are intermediates in the synthesis of various pharmaceuticals and natural products. The easiest way to synthesize this type of compounds is through the addition of acetylenes to carbonyl compounds. A catalytic system for this reaction using Zn(OTf)2 in combination with N,N-dialkylated 1,2-amino alcohol ligands has been reported. Employing cinchona alkaloid ligands, available from the chiral pool, in this catalytic system we have found that the addition of acetylenes to aldehydes is catalyzed at room temperature with ee's up to 89%.
 

Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 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