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

David C. Blakemore; Jean-Yves Chiva; Iain Thistlethwaite

doi:10.1055/s-0030-1259957

LETTER

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;

Abstract

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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

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References

http://data.unaids.org/pub/FactSheet/2009/20091124_FS_global_en.pdf

<A NAME="RD33010ST-2A">2a</A> Barber CG. Blakemore DC. Bioorg. Med. Chem. Lett. 2009, 19: 1075

<A NAME="RD33010ST-2B">2b</A> Barber CG. Blakemore DC. Bioorg. Med. Chem. Lett. 2009, 19: 1499

<A NAME="RD33010ST-3">3</A> O’Brien P. Phillips DW. Towers TD. Tetrahedron Lett. 2002, 43: 7333