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

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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

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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

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Key Words

enantioselective addition, terminal acetylenes, aldehydes, propargyl alcohols

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ID: J54-Y2002-510