Enantioselective [1,2]-Stevens rearrangement using sugar-derived alkoxides as chiral promoters

Katsuhiko Tomooka; Junichiro Sakamaki; Manabu Harada; Ryoji Wada

doi:10.1055/s-2008-1032107

Enantioselective [1,2]-Stevens rearrangement using sugar-derived alkoxides as chiral promoters

Katsuhiko Tomooka, Junichiro Sakamaki, Manabu Harada, Ryoji Wada

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

The first example of enantioselective base-induced [1,2]-Stevens rearrangement was achieved by using the newly developed D-glucose-derived lithium alkoxide as a chiral promoter. This rearrangement provides an α-amino ketone having a pseudoquaternary chiral center in an enantioenriched form.

Original language	English
Pages (from-to)	683-686
Number of pages	4
Journal	Synlett
Issue number	5
DOIs	https://doi.org/10.1055/s-2008-1032107
Publication status	Published - Mar 18 2008

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Enantioselective [1,2]-Stevens rearrangement using sugar-derived alkoxides as chiral promoters",

abstract = "The first example of enantioselective base-induced [1,2]-Stevens rearrangement was achieved by using the newly developed D-glucose-derived lithium alkoxide as a chiral promoter. This rearrangement provides an α-amino ketone having a pseudoquaternary chiral center in an enantioenriched form.",

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AU - Harada, Manabu

AU - Wada, Ryoji

PY - 2008/3/18

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N2 - The first example of enantioselective base-induced [1,2]-Stevens rearrangement was achieved by using the newly developed D-glucose-derived lithium alkoxide as a chiral promoter. This rearrangement provides an α-amino ketone having a pseudoquaternary chiral center in an enantioenriched form.

AB - The first example of enantioselective base-induced [1,2]-Stevens rearrangement was achieved by using the newly developed D-glucose-derived lithium alkoxide as a chiral promoter. This rearrangement provides an α-amino ketone having a pseudoquaternary chiral center in an enantioenriched form.

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Enantioselective [1,2]-Stevens rearrangement using sugar-derived alkoxides as chiral promoters

Abstract

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