Organic Chemistry Portal

Abstracts

Search:

Efficient Enantioselective Additions of Terminal Alkynes and Aldehydes under Operationally Convenient Conditions

Dean Boyall, Doug E. Frantz and Erick M. Carreira*

*Laboratorium für Organische Chemie, ETH-Hoenggerberg HCI H335, CH-8093 Zuerich, Switzerland, Email: carreiraorg.chem.ethz.ch

D. Boyall, D. Frantz, E. M. Carreira, Org. Lett., 2002, 4, 2605-2606.

DOI: 10.1021/ol026282k


Abstract

Enantioselective additions of terminal acetylenes to aldehydes mediated by Zn(OTf)2 and (+)-N-methyl ephedrine can be conducted in reagent grade toluene containing up to 1000 ppm H2O. Products are isolated in high yield and high enantioselectivities.

see article for more examples



Facile Enantioselective Synthesis of Propargylic Alcohols by Direct Addition of Terminal Alkynes to Aldehydes

D. E. Frantz, R. Fässler, E. M. Carreira, J. Am. Chem. Soc., 2000, 122, 1806-1807. DOI: 10.1021/ja993838z


Key Words

enantioselective addition, terminal acetylenes, aldehydes, propargyl alcohols


ID: J54-Y2002-510