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The aza-[2,3]-Wittig sigmatropic rearrangement of Z(C)-alkenes

✍ Scribed by James C Anderson; Philippe Dupau; D Craig Siddons; Stephen C Smith; Martin E Swarbrick

Book ID: 104258982
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 134 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00229-9

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✦ Synopsis

The aza-[2,3]-Wittig sigmatropic rearrangement of Z(C)-alkenes can be achieved through the use of a trimethylsilyl anion stabilising group. The major diastereoisomer complements previous results and allows access to each diastereoisomer of the homoallylic amine products. A transition state model is described which accounts for the diminished diastereoselection compared to E-alkyl substrates.

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