A Highly Stereoselective Synthesis of β-Trifluoromethylated Homoallylic Alchols in Water


  • This research was supported by the National University of Singapore (grant nos. RP 930657, PR 940633, and RP 950609).


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A tin-mediated, indium trichloride promoted allylation reaction provided β-trifluoromethylated homoallylic alcohols, the building blocks of biologically active substances, in high yields and excellent stereoselectivity (see below; R = H, Cy, Ar, COOH). Since the syntheses can be carried out in water, the reactive OH groups do not need to be protected, and even compounds that are insoluble in organic solvents can be used.