Convenient, large-scale asymmetric synthesis of enantiomerically pure trans-cinnamylglycine and -α-alanine

Wei Qiu; Vadim A. Soloshonok; Chaozhong Cai; Xuejun Tang; Victor J. Hruby

doi:10.1016/S0040-4020(00)00176-9

Convenient, large-scale asymmetric synthesis of enantiomerically pure trans-cinnamylglycine and -α-alanine

Wei Qiu, Vadim A. Soloshonok, Chaozhong Cai, Xuejun Tang, Victor J. Hruby

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

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Abstract

Asymmetric syntheses of (S)-trans-cinnamylglycine and (S)-α-trans- cinnamyl-α-alanine via reactions of cinnamyl halides (Cl, Br) with Ni(II)- complexes of the chiral Schiff base of glycine or alanine with (S)-o-[N-(N- benzylprolyl)amino]benzophenone were developed. Inexpensive and readily available reagents and solvents were used, including an easily recyclable chiral auxiliary. The simplicity of the experimental procedures and the high stereochemical outcome make this method synthetically attractive for preparing the target amino acids on multi-gram scales. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	2577-2582
Number of pages	6
Journal	Tetrahedron
Volume	56
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4020(00)00176-9
State	Published - Apr 21 2000
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00176-9

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title = "Convenient, large-scale asymmetric synthesis of enantiomerically pure trans-cinnamylglycine and -α-alanine",

abstract = "Asymmetric syntheses of (S)-trans-cinnamylglycine and (S)-α-trans- cinnamyl-α-alanine via reactions of cinnamyl halides (Cl, Br) with Ni(II)- complexes of the chiral Schiff base of glycine or alanine with (S)-o-[N-(N- benzylprolyl)amino]benzophenone were developed. Inexpensive and readily available reagents and solvents were used, including an easily recyclable chiral auxiliary. The simplicity of the experimental procedures and the high stereochemical outcome make this method synthetically attractive for preparing the target amino acids on multi-gram scales. (C) 2000 Elsevier Science Ltd.",

author = "Wei Qiu and Soloshonok, {Vadim A.} and Chaozhong Cai and Xuejun Tang and Hruby, {Victor J.}",

note = "Funding Information: This work was supported by the grants from US Public Health Service Grant and the National Institute of Drug Abuse DA 06284, DA 04248 and DK 17420. The views expressed are those of the authors and not necessarily of the USPHS.",

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doi = "10.1016/S0040-4020(00)00176-9",

language = "English (US)",

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T1 - Convenient, large-scale asymmetric synthesis of enantiomerically pure trans-cinnamylglycine and -α-alanine

AU - Qiu, Wei

AU - Soloshonok, Vadim A.

AU - Cai, Chaozhong

AU - Tang, Xuejun

AU - Hruby, Victor J.

N1 - Funding Information: This work was supported by the grants from US Public Health Service Grant and the National Institute of Drug Abuse DA 06284, DA 04248 and DK 17420. The views expressed are those of the authors and not necessarily of the USPHS.

PY - 2000/4/21

Y1 - 2000/4/21

N2 - Asymmetric syntheses of (S)-trans-cinnamylglycine and (S)-α-trans- cinnamyl-α-alanine via reactions of cinnamyl halides (Cl, Br) with Ni(II)- complexes of the chiral Schiff base of glycine or alanine with (S)-o-[N-(N- benzylprolyl)amino]benzophenone were developed. Inexpensive and readily available reagents and solvents were used, including an easily recyclable chiral auxiliary. The simplicity of the experimental procedures and the high stereochemical outcome make this method synthetically attractive for preparing the target amino acids on multi-gram scales. (C) 2000 Elsevier Science Ltd.

AB - Asymmetric syntheses of (S)-trans-cinnamylglycine and (S)-α-trans- cinnamyl-α-alanine via reactions of cinnamyl halides (Cl, Br) with Ni(II)- complexes of the chiral Schiff base of glycine or alanine with (S)-o-[N-(N- benzylprolyl)amino]benzophenone were developed. Inexpensive and readily available reagents and solvents were used, including an easily recyclable chiral auxiliary. The simplicity of the experimental procedures and the high stereochemical outcome make this method synthetically attractive for preparing the target amino acids on multi-gram scales. (C) 2000 Elsevier Science Ltd.

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SN - 0040-4020

VL - 56

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JO - Tetrahedron

JF - Tetrahedron

IS - 17

ER -

Convenient, large-scale asymmetric synthesis of enantiomerically pure trans-cinnamylglycine and -α-alanine

Abstract

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