A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate

Yoshio Ito; Takeo Kawabata; Shiro Terashima

doi:10.1016/S0040-4039(00)85317-4

A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate

Yoshio Ito, Takeo Kawabata, Shiro Terashima

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

29 Citations (Scopus)

Abstract

A highly efficient synthesis of the title compound was accomplished employing the addition of diketene to chiral imine as a key stereoselective reaction and using inexpensive (S)-ethy1 lactate as a starting material.

Original language	English
Pages (from-to)	5751-5754
Number of pages	4
Journal	Tetrahedron Letters
Volume	27
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(00)85317-4
Publication status	Published - 1986
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)85317-4

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@article{c23939894cfc4defbd2650f647858e1f,

title = "A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate",

abstract = "A highly efficient synthesis of the title compound was accomplished employing the addition of diketene to chiral imine as a key stereoselective reaction and using inexpensive (S)-ethy1 lactate as a starting material.",

author = "Yoshio Ito and Takeo Kawabata and Shiro Terashima",

year = "1986",

doi = "10.1016/S0040-4039(00)85317-4",

language = "English",

volume = "27",

pages = "5751--5754",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "47",

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TY - JOUR

T1 - A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate

AU - Ito, Yoshio

AU - Kawabata, Takeo

AU - Terashima, Shiro

PY - 1986

Y1 - 1986

N2 - A highly efficient synthesis of the title compound was accomplished employing the addition of diketene to chiral imine as a key stereoselective reaction and using inexpensive (S)-ethy1 lactate as a starting material.

AB - A highly efficient synthesis of the title compound was accomplished employing the addition of diketene to chiral imine as a key stereoselective reaction and using inexpensive (S)-ethy1 lactate as a starting material.

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UR - http://www.scopus.com/inward/citedby.url?scp=0022970513&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)85317-4

DO - 10.1016/S0040-4039(00)85317-4

M3 - Article

AN - SCOPUS:0022970513

SN - 0040-4039

VL - 27

SP - 5751

EP - 5754

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate

Abstract

All Science Journal Classification (ASJC) codes

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