A convenient method for synthesis of trans-4-cyclohexyl-L-proline

Xiao Chen; Da Ming Du; Wen Ting Hua

doi:10.1016/S0957-4166(02)00052-6

A convenient method for synthesis of trans-4-cyclohexyl-L-proline

Xiao Chen
, Da Ming Du
, Wen Ting Hua^*

^*此作品的通讯作者

Peking University

科研成果: 期刊稿件 › 文章 › 同行评审

14 引用（Scopus）

摘要

A convenient method for the synthesis of the fosinopril precursor, trans-4-cyclohexyl-L-proline 1, has been developed. A highly stereoselective alkylation of N-benzyl-pyroglutamic acid 2 with 3-bromocyclohexene at -10°C and subsequent hydrogenolysis afforded the trans-4-cyclohexyl-L-pyroglutamic acid 4. The esterified 4 was sulfurized with Lawesson's reagent, desulfurized with Raney-Ni and hydrogenolytic cleavage of the benzyl protecting groups to afford 1 with 93% e.e.

源语言	英语
页（从-至）	43-46
页数	4
期刊	Tetrahedron Asymmetry
卷	13
期	1
DOI	https://doi.org/10.1016/S0957-4166(02)00052-6
出版状态	已出版 - 13 2月 2002
已对外发布	是

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title = "A convenient method for synthesis of trans-4-cyclohexyl-L-proline",

abstract = "A convenient method for the synthesis of the fosinopril precursor, trans-4-cyclohexyl-L-proline 1, has been developed. A highly stereoselective alkylation of N-benzyl-pyroglutamic acid 2 with 3-bromocyclohexene at -10°C and subsequent hydrogenolysis afforded the trans-4-cyclohexyl-L-pyroglutamic acid 4. The esterified 4 was sulfurized with Lawesson's reagent, desulfurized with Raney-Ni and hydrogenolytic cleavage of the benzyl protecting groups to afford 1 with 93\% e.e.",

author = "Xiao Chen and Du, \{Da Ming\} and Hua, \{Wen Ting\}",

year = "2002",

month = feb,

day = "13",

doi = "10.1016/S0957-4166(02)00052-6",

language = "English",

volume = "13",

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T1 - A convenient method for synthesis of trans-4-cyclohexyl-L-proline

AU - Chen, Xiao

AU - Du, Da Ming

AU - Hua, Wen Ting

PY - 2002/2/13

Y1 - 2002/2/13

N2 - A convenient method for the synthesis of the fosinopril precursor, trans-4-cyclohexyl-L-proline 1, has been developed. A highly stereoselective alkylation of N-benzyl-pyroglutamic acid 2 with 3-bromocyclohexene at -10°C and subsequent hydrogenolysis afforded the trans-4-cyclohexyl-L-pyroglutamic acid 4. The esterified 4 was sulfurized with Lawesson's reagent, desulfurized with Raney-Ni and hydrogenolytic cleavage of the benzyl protecting groups to afford 1 with 93% e.e.

AB - A convenient method for the synthesis of the fosinopril precursor, trans-4-cyclohexyl-L-proline 1, has been developed. A highly stereoselective alkylation of N-benzyl-pyroglutamic acid 2 with 3-bromocyclohexene at -10°C and subsequent hydrogenolysis afforded the trans-4-cyclohexyl-L-pyroglutamic acid 4. The esterified 4 was sulfurized with Lawesson's reagent, desulfurized with Raney-Ni and hydrogenolytic cleavage of the benzyl protecting groups to afford 1 with 93% e.e.

UR - https://www.scopus.com/pages/publications/0037070074

U2 - 10.1016/S0957-4166(02)00052-6

DO - 10.1016/S0957-4166(02)00052-6

M3 - Article

AN - SCOPUS:0037070074

SN - 0957-4166

VL - 13

SP - 43

EP - 46

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 1

ER -

A convenient method for synthesis of trans-4-cyclohexyl-L-proline

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