Catalytic synthesis of peptide-derived thiazolines and oxazolines using bis(quinolinolato)dioxomolybdenum(VI) complexes

Akira Sakakura; Rei Kondo; Shuhei Umemura; Kazuaki Ishihara

doi:10.1002/adsc.200700068

Catalytic synthesis of peptide-derived thiazolines and oxazolines using bis(quinolinolato)dioxomolybdenum(VI) complexes

Akira Sakakura, Rei Kondo, Shuhei Umemura, Kazuaki Ishihara

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

27 Citations (Scopus)

Abstract

Bis(2-ethyl-8-quinolinolato)dioxomolybdenum(VI) (9) (1 mol %) shows remarkable catalytic activity for the dehydrative cyclization of cysteine-containing dipeptides 1 to give the corresponding thiazolines 2 with less than 6 % epimerization at the C2-exomethine position. For the dehydrative cyclization of threonine-containing dipeptides 4, 1 mol % of bis(2-phenyl-8-quinolinolato)dioxomolybdenum(VI) (10) gives the corresponding oxazolines 5 with retention of configuration at the 5-position.

Original language	English
Pages (from-to)	1641-1646
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	349
Issue number	10
DOIs	https://doi.org/10.1002/adsc.200700068
Publication status	Published - Jul 2007
Externally published	Yes

Keywords

Catalysis
Dehydrative cyclization
Molybdenum
Oxazolines
Quinolinolato species
Thiazolines

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200700068

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title = "Catalytic synthesis of peptide-derived thiazolines and oxazolines using bis(quinolinolato)dioxomolybdenum(VI) complexes",

abstract = "Bis(2-ethyl-8-quinolinolato)dioxomolybdenum(VI) (9) (1 mol %) shows remarkable catalytic activity for the dehydrative cyclization of cysteine-containing dipeptides 1 to give the corresponding thiazolines 2 with less than 6 % epimerization at the C2-exomethine position. For the dehydrative cyclization of threonine-containing dipeptides 4, 1 mol % of bis(2-phenyl-8-quinolinolato)dioxomolybdenum(VI) (10) gives the corresponding oxazolines 5 with retention of configuration at the 5-position.",

keywords = "Catalysis, Dehydrative cyclization, Molybdenum, Oxazolines, Quinolinolato species, Thiazolines",

author = "Akira Sakakura and Rei Kondo and Shuhei Umemura and Kazuaki Ishihara",

year = "2007",

month = jul,

doi = "10.1002/adsc.200700068",

language = "English",

volume = "349",

pages = "1641--1646",

journal = "Advanced Synthesis and Catalysis",

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TY - JOUR

T1 - Catalytic synthesis of peptide-derived thiazolines and oxazolines using bis(quinolinolato)dioxomolybdenum(VI) complexes

AU - Sakakura, Akira

AU - Kondo, Rei

AU - Umemura, Shuhei

AU - Ishihara, Kazuaki

PY - 2007/7

Y1 - 2007/7

N2 - Bis(2-ethyl-8-quinolinolato)dioxomolybdenum(VI) (9) (1 mol %) shows remarkable catalytic activity for the dehydrative cyclization of cysteine-containing dipeptides 1 to give the corresponding thiazolines 2 with less than 6 % epimerization at the C2-exomethine position. For the dehydrative cyclization of threonine-containing dipeptides 4, 1 mol % of bis(2-phenyl-8-quinolinolato)dioxomolybdenum(VI) (10) gives the corresponding oxazolines 5 with retention of configuration at the 5-position.

AB - Bis(2-ethyl-8-quinolinolato)dioxomolybdenum(VI) (9) (1 mol %) shows remarkable catalytic activity for the dehydrative cyclization of cysteine-containing dipeptides 1 to give the corresponding thiazolines 2 with less than 6 % epimerization at the C2-exomethine position. For the dehydrative cyclization of threonine-containing dipeptides 4, 1 mol % of bis(2-phenyl-8-quinolinolato)dioxomolybdenum(VI) (10) gives the corresponding oxazolines 5 with retention of configuration at the 5-position.

KW - Catalysis

KW - Dehydrative cyclization

KW - Molybdenum

KW - Oxazolines

KW - Quinolinolato species

KW - Thiazolines

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DO - 10.1002/adsc.200700068

M3 - Article

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SN - 1615-4150

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JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 10

ER -

Catalytic synthesis of peptide-derived thiazolines and oxazolines using bis(quinolinolato)dioxomolybdenum(VI) complexes

Abstract

Keywords

ASJC Scopus subject areas

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