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2005
Stereochemistry
O 0030
Kinetic Resolution of Allylic Alcohols Promoted by Electrophilic Selenium
— The first example of an efficient kinetic resolution using an electrophilic
31- 027 Reagents.
selenium reagent is reported. Racemic allylic alcohol (I) reacts with half an equivalent
of selenylating agent (II) in methanol giving rise to the regiospecific formation of the
corresponding addition product (IV) with a very high level of facial selectivity. The unreacted alcohol can be recovered in an optically enriched form. In the case of
mono-substituted alkenes (V), the facial selectivity is very low. However, the addition
to the double bond proceeds completely regiospecific and only the anti-Markovnikov
regioisomers are obtained. — (SANTI*, C.; TIECCO, M.; TESTAFERRI, L.;
TOMASSINI, C.; MARINI, F.; BAGNOLI, L.; TEMPERINI, A.; Phosphorus, Sulfur
Silicon Relat. Elem. 180 (2005) 3-4, 1071-1075; Dip. Chim., Univ. Perugia, I-06100
Perugia, Italy; Eng.) — F. Santoso
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