Asymmetric Diels-Alder reactions of N-allenoyloxazolidinones catalyzed by Cu(II)-bis(oxazoline) complexes

Torsak Luanphaisarnnont

doi:10.1016/j.tetlet.2014.10.051

Asymmetric Diels-Alder reactions of N-allenoyloxazolidinones catalyzed by Cu(II)-bis(oxazoline) complexes

Torsak Luanphaisarnnont

Mahidol University

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

6 Citations (Scopus)

Abstract

Catalytic asymmetric Diels-Alder reactions of N-allenoyloxazolidinones were investigated. Various chiral metal-bis(oxazoline) and metal-pyridinebis(oxazoline) complexes were screened. Cu(SbF₆)₂(H₂O)₂(t-BuBox) was found to be the most effective catalyst, giving the product in high yield, enantioselectivity, and endo:exo selectivity. The relative reactivity between N-allenoyloxazolidinones and N-alkenoyloxazolidinones was also investigated. A model for stereoinduction was proposed to account for the enantioselectivity and endo:exo selectivity.

Original language	English
Pages (from-to)	6803-6807
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2014.10.051
Publication status	Published - 10 Dec 2014
Externally published	Yes

Keywords

Allenes
Bis(oxazoline)
Diels-Alder cycloaddition
Enantioselective catalysis
Lewis acid catalysis

Access to Document

10.1016/j.tetlet.2014.10.051

Cite this

@article{8b41aae0f86c4c8c881f0e2ade9363f8,

title = "Asymmetric Diels-Alder reactions of N-allenoyloxazolidinones catalyzed by Cu(II)-bis(oxazoline) complexes",

abstract = "Catalytic asymmetric Diels-Alder reactions of N-allenoyloxazolidinones were investigated. Various chiral metal-bis(oxazoline) and metal-pyridinebis(oxazoline) complexes were screened. Cu(SbF6)2(H2O)2(t-BuBox) was found to be the most effective catalyst, giving the product in high yield, enantioselectivity, and endo:exo selectivity. The relative reactivity between N-allenoyloxazolidinones and N-alkenoyloxazolidinones was also investigated. A model for stereoinduction was proposed to account for the enantioselectivity and endo:exo selectivity.",

keywords = "Allenes, Bis(oxazoline), Diels-Alder cycloaddition, Enantioselective catalysis, Lewis acid catalysis",

author = "Torsak Luanphaisarnnont",

year = "2014",

month = dec,

day = "10",

doi = "10.1016/j.tetlet.2014.10.051",

language = "English",

volume = "55",

pages = "6803--6807",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "50",

}

TY - JOUR

T1 - Asymmetric Diels-Alder reactions of N-allenoyloxazolidinones catalyzed by Cu(II)-bis(oxazoline) complexes

AU - Luanphaisarnnont, Torsak

PY - 2014/12/10

Y1 - 2014/12/10

N2 - Catalytic asymmetric Diels-Alder reactions of N-allenoyloxazolidinones were investigated. Various chiral metal-bis(oxazoline) and metal-pyridinebis(oxazoline) complexes were screened. Cu(SbF6)2(H2O)2(t-BuBox) was found to be the most effective catalyst, giving the product in high yield, enantioselectivity, and endo:exo selectivity. The relative reactivity between N-allenoyloxazolidinones and N-alkenoyloxazolidinones was also investigated. A model for stereoinduction was proposed to account for the enantioselectivity and endo:exo selectivity.

AB - Catalytic asymmetric Diels-Alder reactions of N-allenoyloxazolidinones were investigated. Various chiral metal-bis(oxazoline) and metal-pyridinebis(oxazoline) complexes were screened. Cu(SbF6)2(H2O)2(t-BuBox) was found to be the most effective catalyst, giving the product in high yield, enantioselectivity, and endo:exo selectivity. The relative reactivity between N-allenoyloxazolidinones and N-alkenoyloxazolidinones was also investigated. A model for stereoinduction was proposed to account for the enantioselectivity and endo:exo selectivity.

KW - Allenes

KW - Bis(oxazoline)

KW - Diels-Alder cycloaddition

KW - Enantioselective catalysis

KW - Lewis acid catalysis

UR - https://www.scopus.com/pages/publications/84910678550

U2 - 10.1016/j.tetlet.2014.10.051

DO - 10.1016/j.tetlet.2014.10.051

M3 - Article

AN - SCOPUS:84910678550

SN - 0040-4039

VL - 55

SP - 6803

EP - 6807

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Asymmetric Diels-Alder reactions of N-allenoyloxazolidinones catalyzed by Cu(II)-bis(oxazoline) complexes

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this