HIGHLY SELECTIVE γ-ALKYLATION OF TRIISOPROPYLSILYLALLYL ANION. SYNTHESIS OF α-TRIISOPROPYLSILYL ALDEHYDES.

DOI: 10.1016/S0040-4039(00)98211-X

Source and publish data:

Tetrahedron Letters p. 5375 - 5378 (1985)

Update date:2022-08-02

Topics:

Authors:

Muchowski, Joseph M.

Naef, Reto

Maddox, Michael L.

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Article abstract of DOI:10.1016/S0040-4039(00)98211-X

The reaction of triisopropylsilylallyllithium with alkyl halides took place with considerably greater γ-selectivity than reported for trimethylsilyl allyllithium.Silica gel induced rearrangement of the epoxides 5 derived from the alkylation products 3 gave α-triisopropylsilyl aldehydes 6 by a process in which silyl group transposition occurred with predominant inversion at the migration terminus.

Full text of DOI:10.1016/S0040-4039(00)98211-X

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