Abstract
Successive treatment of ( E)-Cα,Cβ-disubstltuted N-enoyl sultams 6 and 13 with organocopper reagents (Me 2CuLi, (CH 2CH) 2CuLi, Ph 2CuLi in the presence of PBu 3 or SCN −) and aq. NH 4Cl gave products 7 and 14. respectivety, with good to excellent stereoface differentiation at Cβ and Cα. Crystallization and mild saponification 7 → 11 and 14 → 15 furnished enantiomerically pure carboxylic acids containing two new stereogenic centers. The postulated reaction topology is supported via acetylatlon of the transient “nolate” ( 22 → 23 ) and compared with that of the related organomagnesium- addition/protonation sequence.
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