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Synlett 2011(8): 1101-1104  
DOI: 10.1055/s-0030-1259957
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rearrangement of 1-Phenylbutane-1,3-diamines via an Azetidinium Cation Intermediate

David C. Blakemore, Jean-Yves Chiva*, Iain Thistlethwaite
Sandwich Chemistry, Pfizer Global Research and Development, Ramsgate Road, Sandwich, Kent, CT13 9NJ, UK
e-Mail: Jean-Yves.Chiva@Pfizer.com;
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Publication History

Received 8 March 2011
Publication Date:
18 April 2011 (online)

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Abstract

Treatment of 4-amino-4-phenyl-butan-2-ol with mesyl chloride, followed by displacement with amine nucleophiles resulted in a 1,3 rearrangement via an azetidinium cation intermediate. This rearrangement has been proven to proceed via a double inversion of stereocentres at positions 1 and 3.

Key words

amines - azetidinium cation - double inversion - nucleophiles - rearrangement

    References

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