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Issue 52, 2014
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Double axial chirality promoted asymmetric [2,3] Stevens rearrangement of N-cinnamyl L-alanine amide-derived ammonium ylides

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Abstract

The base-induced asymmetric [2,3] Stevens rearrangement of N-cinnamyl tetraalkylammonium ylides derived from L-alanine amides proceeds via a double axially chiral intermediate to afford the corresponding α-substituted alanine derivatives with high enantio- and diastereoselectivities.

Graphical abstract: Double axial chirality promoted asymmetric [2,3] Stevens rearrangement of N-cinnamyl l-alanine amide-derived ammonium ylides

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Publication details

The article was received on 07 Apr 2014, accepted on 01 May 2014 and first published on 06 May 2014


Article type: Communication
DOI: 10.1039/C4CC02536A
Citation: Chem. Commun., 2014,50, 6860-6862
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    Double axial chirality promoted asymmetric [2,3] Stevens rearrangement of N-cinnamyl L-alanine amide-derived ammonium ylides

    E. Tayama, N. Naganuma, H. Iwamoto and E. Hasegawa, Chem. Commun., 2014, 50, 6860
    DOI: 10.1039/C4CC02536A

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