Asymmetric synthesis of all four isomers of topographically constrained novel amino acids: β-isopropyltyrosines

Jun Lin; Subo Liao; Yinglin Han; Wei Qiu; Victor J. Hruby

doi:10.1016/S0957-4166(97)00381-9

Asymmetric synthesis of all four isomers of topographically constrained novel amino acids: β-isopropyltyrosines

Jun Lin
, Subo Liao
, Yinglin Han
, Wei Qiu
, Victor J. Hruby

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

26 Scopus citations

Abstract

All four stereoisomers of the highly constrained novel amino acid, β-isopropyltyrosine, have been synthesized with high stereoselectivities (>90% de) and in 40-50% overall yields by using the optically pure 4-phenyloxazolidinone as a chiral auxiliary via asymmetric Michael addition, direct or indirect azidation, hydrogenolysis and demethylation reactions.

Original language	English (US)
Pages (from-to)	3213-3221
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	8
Issue number	19
DOIs	https://doi.org/10.1016/S0957-4166(97)00381-9
State	Published - Oct 1997
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/S0957-4166(97)00381-9

Cite this

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title = "Asymmetric synthesis of all four isomers of topographically constrained novel amino acids: β-isopropyltyrosines",

abstract = "All four stereoisomers of the highly constrained novel amino acid, β-isopropyltyrosine, have been synthesized with high stereoselectivities (>90\% de) and in 40-50\% overall yields by using the optically pure 4-phenyloxazolidinone as a chiral auxiliary via asymmetric Michael addition, direct or indirect azidation, hydrogenolysis and demethylation reactions.",

author = "Jun Lin and Subo Liao and Yinglin Han and Wei Qiu and Hruby, \{Victor J.\}",

note = "Funding Information: This work has been supported by NIDA Grants DA 06284 and DA 04248, and U.S. Public Health Service Grant DK 17420. The contents are the responsibility of the authors and do not necessarily reflect the official views of the US PHS.",

year = "1997",

month = oct,

doi = "10.1016/S0957-4166(97)00381-9",

language = "English (US)",

volume = "8",

pages = "3213--3221",

journal = "Tetrahedron Asymmetry",

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TY - JOUR

T1 - Asymmetric synthesis of all four isomers of topographically constrained novel amino acids

T2 - β-isopropyltyrosines

AU - Lin, Jun

AU - Liao, Subo

AU - Han, Yinglin

AU - Qiu, Wei

AU - Hruby, Victor J.

N1 - Funding Information: This work has been supported by NIDA Grants DA 06284 and DA 04248, and U.S. Public Health Service Grant DK 17420. The contents are the responsibility of the authors and do not necessarily reflect the official views of the US PHS.

PY - 1997/10

Y1 - 1997/10

N2 - All four stereoisomers of the highly constrained novel amino acid, β-isopropyltyrosine, have been synthesized with high stereoselectivities (>90% de) and in 40-50% overall yields by using the optically pure 4-phenyloxazolidinone as a chiral auxiliary via asymmetric Michael addition, direct or indirect azidation, hydrogenolysis and demethylation reactions.

AB - All four stereoisomers of the highly constrained novel amino acid, β-isopropyltyrosine, have been synthesized with high stereoselectivities (>90% de) and in 40-50% overall yields by using the optically pure 4-phenyloxazolidinone as a chiral auxiliary via asymmetric Michael addition, direct or indirect azidation, hydrogenolysis and demethylation reactions.

UR - https://www.scopus.com/pages/publications/0030858104

UR - https://www.scopus.com/pages/publications/0030858104#tab=citedBy

U2 - 10.1016/S0957-4166(97)00381-9

DO - 10.1016/S0957-4166(97)00381-9

M3 - Article

AN - SCOPUS:0030858104

SN - 0957-4166

VL - 8

SP - 3213

EP - 3221

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 19

ER -

Asymmetric synthesis of all four isomers of topographically constrained novel amino acids: β-isopropyltyrosines

Abstract

ASJC Scopus subject areas

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