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

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

Research output: Contribution to journalArticle

27 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2137-2140
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number12
DOIs
StatePublished - Mar 18 2002

Fingerprint

Boronic Acids
Aromatic Amino Acids
Hydrogenation
Phenylalanine
Derivatives
Amino Acids
Enantioselectivity
Carboxylic acids
Catalysts

Keywords

  • Asymmetric hydrogenation
  • Constrained amino acids
  • DuPHOS
  • Naphthylalanine
  • Phenylalanine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives. / Wang, Wei; Zhang, Junyi; Xiong, Chiyi; Hruby, Victor J.

In: Tetrahedron Letters, Vol. 43, No. 12, 18.03.2002, p. 2137-2140.

Research output: Contribution to journalArticle

@article{d3594b3ed0c94648b3e2a3c94c3d16d7,
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}",
year = "2002",
month = "3",
day = "18",
doi = "10.1016/S0040-4039(02)00249-6",
language = "English (US)",
volume = "43",
pages = "2137--2140",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "12",

}

TY - JOUR

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

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

UR - http://www.scopus.com/inward/record.url?scp=0037128493&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037128493&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(02)00249-6

DO - 10.1016/S0040-4039(02)00249-6

M3 - Article

AN - SCOPUS:0037128493

VL - 43

SP - 2137

EP - 2140

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 12

ER -