Facile conversion of CF3-containing propargylic alcohol derivatives via the corresponding allenes

作者：Yamazaki Takashi^*; Watanabe Yohsuke; Yoshida Nao; Kawasaki Takasuka Tomoko

来源：Tetrahedron, 2012, 68(33): 6665-6673.

DOI：10.1016/j.tet.2012.05.131

• Propargylic alcohols
• Trifluoromethyl group
• Allenes
• alpha,beta-Unsaturated ketones
• Stereoselectivity

Empirical information on the acidity of the propargylic proton from our previous work allowed us to develop novel synthetic transformations of readily available terminally trifluoromethylated propargylic alcohols 1 into the corresponding allenyl tosylates 3a, 1-tosyloxy- or 1-acyloxy-4,4,4-trifluorobutan-2-ones 4, and 2-(2,2,2-trifluoroethyl)prop-2-en-1-ones 5, which was enabled by such common bases as NaOH and tertiary amines for affecting ready abstraction of this proton.

• 出版日期2012-8-19