A highly regio-, diastereo-, and enantioselective desymmetrization of five-, six-, and seven-membered meso-cyclic allylic bis-diethyl phosphates (2a, 2b, and 2c, respectively) was obtained with diethylzinc, using catalytic amounts of [Cu(OTf)](2).C6H6 and phosphoramidite ligands 5. Enantiomeric excesses of up to 87, 94, and >98% were obtained for the addition of diethylzinc to cyclopentene, cyclohexene, and cycloheptene bis-diethyl phosphates, respectively.
Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates / U. Piarulli, C. Claverie, P. Daubos, C.M.A. Gennari, A.J. Minnaard, B.L. Feringa. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 5:23(2003), pp. 4493-4496.
Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates
P. Daubos;C.M.A. Gennari;
2003
Abstract
A highly regio-, diastereo-, and enantioselective desymmetrization of five-, six-, and seven-membered meso-cyclic allylic bis-diethyl phosphates (2a, 2b, and 2c, respectively) was obtained with diethylzinc, using catalytic amounts of [Cu(OTf)](2).C6H6 and phosphoramidite ligands 5. Enantiomeric excesses of up to 87, 94, and >98% were obtained for the addition of diethylzinc to cyclopentene, cyclohexene, and cycloheptene bis-diethyl phosphates, respectively.
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