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Scientific article
English

Asymmetric 1,4-additions of Gilman reagents to α,β - disubstituted (E)-enoylsultams / “enolate” protonations

Published inTetrahedron, vol. 45, no. 2, p. 479-488
Publication date1989
Abstract

Successive treatment of (E)-Cα,Cβ-disubstltuted N-enoyl sultams 6 and 13 with organocopper reagents (Me₂CuLi, (CH₂-CH)₂CuLi, Ph₂CuLi in the presence of PBu₃ or SCN⁻) and aq. NH₄Cl 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 “enolate” (22 → 23) and compared with that of the related organomagnesium- addition/protonation sequence.

Citation (ISO format)
VON OPPOLZER, Wolfgang, KINGMA, Arend Jouke, POLI, Giovanni. Asymmetric 1,4-additions of Gilman reagents to α,β - disubstituted (<i>E</i>)-enoylsultams / “enolate” protonations. In: Tetrahedron, 1989, vol. 45, n° 2, p. 479–488. doi: 10.1016/0040-4020(89)80075-4
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ISSN of the journal0040-4020
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