Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

Sang Hyeup Lee; Xin Qi; Juyoung Yoon; Kensuke Nakamura; Yoon Sik Lee

doi:10.1016/S0040-4020(02)00175-8

Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

Sang Hyeup Lee, Xin Qi, Juyoung Yoon, Kensuke Nakamura, Yoon Sik Lee

Department of Chemistry & Nanoscience

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

18 Scopus citations

Abstract

Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.

Original language	English
Pages (from-to)	2777-2787
Number of pages	11
Journal	Tetrahedron
Volume	58
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4020(02)00175-8
State	Published - 1 Apr 2002

Bibliographical note

Funding Information:
Financial support from the Korean Research Foundation (2000-042-D00044) is gratefully acknowledged.

Keywords

3-amino-2-mercapto acid
Oxazoline
Sharpless asymmetric aminohydroxylation
Taxol

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10.1016/S0040-4020(02)00175-8

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title = "Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine",

abstract = "Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.",

keywords = "3-amino-2-mercapto acid, Oxazoline, Sharpless asymmetric aminohydroxylation, Taxol",

author = "Lee, {Sang Hyeup} and Xin Qi and Juyoung Yoon and Kensuke Nakamura and Lee, {Yoon Sik}",

note = "Funding Information: Financial support from the Korean Research Foundation (2000-042-D00044) is gratefully acknowledged. ",

year = "2002",

month = apr,

day = "1",

doi = "10.1016/S0040-4020(02)00175-8",

language = "English",

volume = "58",

pages = "2777--2787",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "14",

}

Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine. / Lee, Sang Hyeup; Qi, Xin; Yoon, Juyoung et al.
In: Tetrahedron, Vol. 58, No. 14, 01.04.2002, p. 2777-2787.

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

TY - JOUR

T1 - Preparation of β-amino-α-mercapto acids and amides

T2 - Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

AU - Lee, Sang Hyeup

AU - Qi, Xin

AU - Yoon, Juyoung

AU - Nakamura, Kensuke

AU - Lee, Yoon Sik

N1 - Funding Information: Financial support from the Korean Research Foundation (2000-042-D00044) is gratefully acknowledged.

PY - 2002/4/1

Y1 - 2002/4/1

N2 - Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.

AB - Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.

KW - 3-amino-2-mercapto acid

KW - Oxazoline

KW - Sharpless asymmetric aminohydroxylation

KW - Taxol

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U2 - 10.1016/S0040-4020(02)00175-8

DO - 10.1016/S0040-4020(02)00175-8

M3 - Article

AN - SCOPUS:0036532284

SN - 0040-4020

VL - 58

SP - 2777

EP - 2787

JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -

Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

Abstract

Bibliographical note

Keywords

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