Tetrahedron

Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation—base catalyzed elimination sequence

EV Boltukhina, AE Sheshenev, IM Lyapkalo

Index: Boltukhina, Ekaterina V.; Sheshenev, Andrey E.; Lyapkalo, Ilya M. Tetrahedron, 2011 , vol. 67, # 30 p. 5382 - 5388

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Citation Number: 7

Abstract

Abstract Keto aldehydes were selectively converted to non-conjugated alkynyl ketones possessing an unsubstituted alkyne terminus using one-pot nonaflation—base catalyzed elimination reaction sequences. Consecutive one-pot nonaflation of keto aldehydes with perfluorobutane-1-sulfonyl fluoride and elimination of the nonaflyl group using the P 1 phosphazene base resulted in the formation of a terminal C triple bond; length of mdash