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2005
Dioxole derivatives
R 0170
Stereoselective TiCl4-Promoted Nucleophilic Substitution at C-2 of
— It is found that the
21- 125 (4S,5S)-2-Alkyl-4-methyl-5-trifluoromethyl-1,3-dioxolanes.
Ti-mediated nucleophilic substitution of the dioxolanes (III) and (IV) proceeds with
complete regioselectivity and high stereoselectivity. Treatment with Et3SiD followed
by removal of the auxiliary leads to chiral deuterated alcohols and homoallylic alcohols
which are potent synthons. — (MORELLI*, C. F.; DURI, L.; SALADINO, A.;
SPERANZA, G.; MANITTO, P.; Synthesis 2004, 18, 3005-3010; Dip. Chim. Org.
Ind., Univ. Stud. Milano, CNR, I-20133 Milano, Italy; Eng.) — Jannicke
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