Stevens Rearrangement of a Cyclic Hemiacetal System: Diastereoselective Approach to Chiral α-Amino Ketone

Manabu Harada; Takeshi Nakai; Katsuhiko Tomooka

doi:10.1055/s-2003-44998

Stevens Rearrangement of a Cyclic Hemiacetal System: Diastereoselective Approach to Chiral α-Amino Ketone

Manabu Harada, Takeshi Nakai, Katsuhiko Tomooka

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

8 Citations (Scopus)

Abstract

The base-promoted reaction of ammonium ylide 1a, which forms a cyclic hemiacetal structure, is shown to afford the anti-hemiacetal 3a in high diastereopurity, via the Stevens rearrangement followed by efficient thermodynamic epimerization.

Original language	English
Pages (from-to)	365-367
Number of pages	3
Journal	Synlett
Issue number	2
DOIs	https://doi.org/10.1055/s-2003-44998
Publication status	Published - Feb 2 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-2003-44998

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title = "Stevens Rearrangement of a Cyclic Hemiacetal System: Diastereoselective Approach to Chiral α-Amino Ketone",

abstract = "The base-promoted reaction of ammonium ylide 1a, which forms a cyclic hemiacetal structure, is shown to afford the anti-hemiacetal 3a in high diastereopurity, via the Stevens rearrangement followed by efficient thermodynamic epimerization.",

author = "Manabu Harada and Takeshi Nakai and Katsuhiko Tomooka",

year = "2004",

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doi = "10.1055/s-2003-44998",

language = "English",

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AU - Harada, Manabu

AU - Nakai, Takeshi

AU - Tomooka, Katsuhiko

PY - 2004/2/2

Y1 - 2004/2/2

N2 - The base-promoted reaction of ammonium ylide 1a, which forms a cyclic hemiacetal structure, is shown to afford the anti-hemiacetal 3a in high diastereopurity, via the Stevens rearrangement followed by efficient thermodynamic epimerization.

AB - The base-promoted reaction of ammonium ylide 1a, which forms a cyclic hemiacetal structure, is shown to afford the anti-hemiacetal 3a in high diastereopurity, via the Stevens rearrangement followed by efficient thermodynamic epimerization.

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U2 - 10.1055/s-2003-44998

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M3 - Article

AN - SCOPUS:1342312170

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JO - Synlett

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IS - 2

ER -

Stevens Rearrangement of a Cyclic Hemiacetal System: Diastereoselective Approach to Chiral α-Amino Ketone

Abstract

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