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Synlett 2011(8): 1101-1104
DOI: 10.1055/s-0030-1259957
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
Further Information
Received
8 March 2011
Publication Date:
18 April 2011 (online)
Publication History
Publication Date:
18 April 2011 (online)
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
-
2a
Barber CG.Blakemore DC. Bioorg. Med. Chem. Lett. 2009, 19: 1075 -
2b
Barber CG.Blakemore DC. Bioorg. Med. Chem. Lett. 2009, 19: 1499 - 3
O’Brien P.Phillips DW.Towers TD. Tetrahedron Lett. 2002, 43: 7333
References
http://data.unaids.org/pub/FactSheet/2009/20091124_FS_global_en.pdf