Issue 12, 1993

Aza-Wittig rearrangements and cyclizations by transmetallation of N-benzylaminomethylstannanes

Abstract

Transmetallation of N-allyl-N-benzylaminomethylstannanes with butyllithium or methyllithium allows carbon–carbon bond formation by a [1, 2]-rearrangement. Substantial amounts of the protodestannylated product are also produced. Transmetallation of the corresponding α-methyl substituted allylic amine or homoallylic amine gives an overall rearrangement by cyclization onto the olefin followed by recapture of the new carbanion by tetramethyltin.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 1275-1276

Aza-Wittig rearrangements and cyclizations by transmetallation of N-benzylaminomethylstannanes

I. Coldham, J. Chem. Soc., Perkin Trans. 1, 1993, 1275 DOI: 10.1039/P19930001275

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