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alpha-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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alpha-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights. / Calvet, Geraldine; Coote, Susannah C.; Blanchard, Nicolas et al.
In: Tetrahedron, Vol. 66, No. 16, 17.04.2010, p. 2969-2980.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Calvet, G, Coote, SC, Blanchard, N & Kouklovsky, C 2010, 'alpha-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights', Tetrahedron, vol. 66, no. 16, pp. 2969-2980. https://doi.org/10.1016/j.tet.2010.02.065

APA

Calvet, G., Coote, S. C., Blanchard, N., & Kouklovsky, C. (2010). alpha-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights. Tetrahedron, 66(16), 2969-2980. https://doi.org/10.1016/j.tet.2010.02.065

Vancouver

Calvet G, Coote SC, Blanchard N, Kouklovsky C. alpha-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights. Tetrahedron. 2010 Apr 17;66(16):2969-2980. doi: 10.1016/j.tet.2010.02.065

Author

Calvet, Geraldine ; Coote, Susannah C. ; Blanchard, Nicolas et al. / alpha-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions : mechanistic insights. In: Tetrahedron. 2010 ; Vol. 66, No. 16. pp. 2969-2980.

Bibtex

@article{86f63ae5c9b340c59fb8603a91294a06,
title = "alpha-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights",
abstract = "alpha-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a beta-oxygenated moiety led to a domino [4+2] cycloaddition/sigma(N-O) bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the sigma(N-O) bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported. (C) 2010 Elsevier Ltd. All rights reserved.",
keywords = "ACYL-NITROSO COMPOUNDS, LEAD TETRAACETATE OXIDATION, N-O BOND, ASYMMETRIC DIELS, HYDROXAMIC ACID, STEREOSELECTIVE CYCLOADDITIONS, ACYLNITROSO DIENOPHILES, CHLORONITROSO COMPOUNDS, REDUCTIVE CLEAVAGE, IMINIUM CATALYSIS",
author = "Geraldine Calvet and Coote, {Susannah C.} and Nicolas Blanchard and Cyrille Kouklovsky",
year = "2010",
month = apr,
day = "17",
doi = "10.1016/j.tet.2010.02.065",
language = "English",
volume = "66",
pages = "2969--2980",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "16",

}

RIS

TY - JOUR

T1 - alpha-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions

T2 - mechanistic insights

AU - Calvet, Geraldine

AU - Coote, Susannah C.

AU - Blanchard, Nicolas

AU - Kouklovsky, Cyrille

PY - 2010/4/17

Y1 - 2010/4/17

N2 - alpha-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a beta-oxygenated moiety led to a domino [4+2] cycloaddition/sigma(N-O) bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the sigma(N-O) bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported. (C) 2010 Elsevier Ltd. All rights reserved.

AB - alpha-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a beta-oxygenated moiety led to a domino [4+2] cycloaddition/sigma(N-O) bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the sigma(N-O) bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported. (C) 2010 Elsevier Ltd. All rights reserved.

KW - ACYL-NITROSO COMPOUNDS

KW - LEAD TETRAACETATE OXIDATION

KW - N-O BOND

KW - ASYMMETRIC DIELS

KW - HYDROXAMIC ACID

KW - STEREOSELECTIVE CYCLOADDITIONS

KW - ACYLNITROSO DIENOPHILES

KW - CHLORONITROSO COMPOUNDS

KW - REDUCTIVE CLEAVAGE

KW - IMINIUM CATALYSIS

U2 - 10.1016/j.tet.2010.02.065

DO - 10.1016/j.tet.2010.02.065

M3 - Journal article

VL - 66

SP - 2969

EP - 2980

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 16

ER -