(R)-2-Phenylglycine as a chiral auxiliary in the asymmetric synthesis of 2-azetidinones

H.L. Van Maanen; J.T.B.H. Jastrzebski; J. Verweij; A.P.G. Kieboom; A.L. Spek; G. Van Koten

doi:10.1016/S0957-4166(00)80336-5

(R)-2-Phenylglycine as a chiral auxiliary in the asymmetric synthesis of 2-azetidinones

H.L. Van Maanen, J.T.B.H. Jastrzebski, J. Verweij, A.P.G. Kieboom, A.L. Spek, G. Van Koten

Sub Organic Chemistry and Catalysis

External unknown

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

Abstract

The chlorozinc enolate of ethyl-[(2,2,5,5-tetramethyl-1-aza-2,5-disila)cyclopentyl]acetate was reacted with the ZnCl2complex of N-benzylidene-2-phenylglycine methyl ester in THF at -70°C. After removal of the protecting silyl moiety (3S, 4S, αR)-1-(methoxycarbonyl)(phenyl)methyl-3-amino-4-phenyl-2-azetidinone was obtained in 73% yield with >97% d.e.. By treatment with aqueous ammonia complete epimerization at the α-position was accomplished. The (3S, 4S, αS) enantiomer was crystallized from THF and the absolute configuration was determined by X-Ray crystallography.

Original language	English
Pages (from-to)	1441-1444
Number of pages	4
Journal	Tetrahedron-Asymmetry
Volume	4
Issue number	7
DOIs	https://doi.org/10.1016/S0957-4166(00)80336-5
Publication status	Published - 12 Mar 1993

Keywords

azetidinone derivative
article
drug synthesis
reaction analysis
X ray crystallography

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10.1016/S0957-4166(00)80336-5

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@article{5c7cb57fa871453ea234bf1661f1cbfc,

title = "(R)-2-Phenylglycine as a chiral auxiliary in the asymmetric synthesis of 2-azetidinones",

abstract = "The chlorozinc enolate of ethyl-[(2,2,5,5-tetramethyl-1-aza-2,5-disila)cyclopentyl]acetate was reacted with the ZnCl2complex of N-benzylidene-2-phenylglycine methyl ester in THF at -70°C. After removal of the protecting silyl moiety (3S, 4S, αR)-1-(methoxycarbonyl)(phenyl)methyl-3-amino-4-phenyl-2-azetidinone was obtained in 73% yield with >97% d.e.. By treatment with aqueous ammonia complete epimerization at the α-position was accomplished. The (3S, 4S, αS) enantiomer was crystallized from THF and the absolute configuration was determined by X-Ray crystallography.",

keywords = "azetidinone derivative, article, drug synthesis, reaction analysis, X ray crystallography",

author = "{Van Maanen}, H.L. and J.T.B.H. Jastrzebski and J. Verweij and A.P.G. Kieboom and A.L. Spek and {Van Koten}, G.",

year = "1993",

month = mar,

day = "12",

doi = "10.1016/S0957-4166(00)80336-5",

language = "English",

volume = "4",

pages = "1441--1444",

journal = "Tetrahedron-Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd",

number = "7",

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TY - JOUR

T1 - (R)-2-Phenylglycine as a chiral auxiliary in the asymmetric synthesis of 2-azetidinones

AU - Van Maanen, H.L.

AU - Jastrzebski, J.T.B.H.

AU - Verweij, J.

AU - Kieboom, A.P.G.

AU - Spek, A.L.

AU - Van Koten, G.

PY - 1993/3/12

Y1 - 1993/3/12

N2 - The chlorozinc enolate of ethyl-[(2,2,5,5-tetramethyl-1-aza-2,5-disila)cyclopentyl]acetate was reacted with the ZnCl2complex of N-benzylidene-2-phenylglycine methyl ester in THF at -70°C. After removal of the protecting silyl moiety (3S, 4S, αR)-1-(methoxycarbonyl)(phenyl)methyl-3-amino-4-phenyl-2-azetidinone was obtained in 73% yield with >97% d.e.. By treatment with aqueous ammonia complete epimerization at the α-position was accomplished. The (3S, 4S, αS) enantiomer was crystallized from THF and the absolute configuration was determined by X-Ray crystallography.

AB - The chlorozinc enolate of ethyl-[(2,2,5,5-tetramethyl-1-aza-2,5-disila)cyclopentyl]acetate was reacted with the ZnCl2complex of N-benzylidene-2-phenylglycine methyl ester in THF at -70°C. After removal of the protecting silyl moiety (3S, 4S, αR)-1-(methoxycarbonyl)(phenyl)methyl-3-amino-4-phenyl-2-azetidinone was obtained in 73% yield with >97% d.e.. By treatment with aqueous ammonia complete epimerization at the α-position was accomplished. The (3S, 4S, αS) enantiomer was crystallized from THF and the absolute configuration was determined by X-Ray crystallography.

KW - azetidinone derivative

KW - article

KW - drug synthesis

KW - reaction analysis

KW - X ray crystallography

U2 - 10.1016/S0957-4166(00)80336-5

DO - 10.1016/S0957-4166(00)80336-5

M3 - Article

SN - 0957-4166

VL - 4

SP - 1441

EP - 1444

JO - Tetrahedron-Asymmetry

JF - Tetrahedron-Asymmetry

IS - 7

ER -

(R)-2-Phenylglycine as a chiral auxiliary in the asymmetric synthesis of 2-azetidinones

Abstract

Keywords

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