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2005
Alcohols
Q 0230
31- 090
Highly Selective 1,3-Isomerization of Allylic Alcohols via Rhenium Oxo Catalysis.
— By use of perrhenate catalyst ReO3-O-SiPh3, allylic alcohols (I) undergo 1,3-isomerization to give the products in high yields and (E)-selectivities. A more general
isomerization procedure is applied to tertiary alcohols (IV) and (VII). It employs BSA
as promoter. Because silylation by BSA is faster for primary than for tertiary alcohols,
the products are irreversibly silylated and removed from the reaction equilibrium.
Subsequent deprotection affords isomerized alcohols in high yields. The chirality of
nonracemic alcohols is transferred with only a small loss of enantiopurity at low temperature. — (MORRILL, C.; GRUBBS*, R. H.; J. Am. Chem. Soc. 127 (2005) 9,
2842-2843; Arnold and Mabel Beckman Lab. Chem. Synth., Calif. Inst. Technol.,
Pasadena, CA 91125, USA; Eng.) — Klein
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