Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives

Wei Wang; Junyi Zhang; Chiyi Xiong; Victor J Hruby

doi:10.1016/S0040-4039(02)00249-6

Design and synthesis of hydrophobic, bulky χ²-constrained phenylalanine and naphthylalanine derivatives

Wei Wang, Junyi Zhang, Chiyi Xiong, Victor J Hruby

Pharmacology and Toxicology

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

27 Scopus citations

Abstract

A series of novel hydrophobic, bulky χ²-constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically pure α-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and with high enantioselectivity.

Original language	English (US)
Pages (from-to)	2137-2140
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4039(02)00249-6
State	Published - Mar 18 2002

Keywords

Asymmetric hydrogenation
Constrained amino acids
DuPHOS
Naphthylalanine
Phenylalanine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(02)00249-6

Cite this

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title = "Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives",

abstract = "A series of novel hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically pure α-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and with high enantioselectivity.",

keywords = "Asymmetric hydrogenation, Constrained amino acids, DuPHOS, Naphthylalanine, Phenylalanine",

author = "Wei Wang and Junyi Zhang and Chiyi Xiong and Hruby, {Victor J}",

note = "Funding Information: This work is supported by US Public Health Service (DK 17420) and the National Institute of Drug Abuse (DA 06284). We also thank Professor Dominic V. McGrath for the use of his group's polarimeter and Professor Michael P. Doyle and Dr. Ming Yan for the use of their chiral HPLC column and assistance. The views expressed are those of the authors and not necessary those of the USPHS.",

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T1 - Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives

AU - Wang, Wei

AU - Zhang, Junyi

AU - Xiong, Chiyi

AU - Hruby, Victor J

N1 - Funding Information: This work is supported by US Public Health Service (DK 17420) and the National Institute of Drug Abuse (DA 06284). We also thank Professor Dominic V. McGrath for the use of his group's polarimeter and Professor Michael P. Doyle and Dr. Ming Yan for the use of their chiral HPLC column and assistance. The views expressed are those of the authors and not necessary those of the USPHS.

PY - 2002/3/18

Y1 - 2002/3/18

N2 - A series of novel hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically pure α-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and with high enantioselectivity.

AB - A series of novel hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically pure α-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and with high enantioselectivity.

KW - Asymmetric hydrogenation

KW - Constrained amino acids

KW - DuPHOS

KW - Naphthylalanine

KW - Phenylalanine

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