Tetrahedron Letters

, том 25 , издание 50 , страницы 5739-5742

The importance of vinylsilane stereochemistry and σ - π stabilization in iminium ion-vinylsilane cyclizations. A short total synthesis of the alkaloid (−) −epielwesine.

Тип публикации: Journal Article

Дата публикации: 1984-01-01

Elsevier

Tetrahedron Letters

scimago Q3

wos Q3

БС2

SJR: 0.334

CiteScore: 3.2

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/S0040-4039(01)81674-9

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Organic Chemistry

Drug Discovery

Biochemistry

Краткое описание

cis -3a-Aryl-2,3,3a,4,5,7a-hexahydro-1H-indoles 5 and 10 are formed in excellent yield from acid promoted cyclization of (Z)-vinylsilane imines 3 and 9. The failure of the corresponding (E)-vinylsilane isomer 4 to cyclize under similar conditions demonstrates that the β-silylcation intermediates formed in these reactions derive significant stabilization from σ - π delocalization.

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ГОСТ |

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Overman L. E. et al. The importance of vinylsilane stereochemistry and σ - π stabilization in iminium ion-vinylsilane cyclizations. A short total synthesis of the alkaloid (−) −epielwesine. // Tetrahedron Letters. 1984. Vol. 25. No. 50. pp. 5739-5742.

ГОСТ со всеми авторами (до 50) Скопировать

Overman L. E., Burk R. D. The importance of vinylsilane stereochemistry and σ - π stabilization in iminium ion-vinylsilane cyclizations. A short total synthesis of the alkaloid (−) −epielwesine. // Tetrahedron Letters. 1984. Vol. 25. No. 50. pp. 5739-5742.

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TY - JOUR

DO - 10.1016/S0040-4039(01)81674-9

UR - https://doi.org/10.1016/S0040-4039(01)81674-9

TI - The importance of vinylsilane stereochemistry and σ - π stabilization in iminium ion-vinylsilane cyclizations. A short total synthesis of the alkaloid (−) −epielwesine.

T2 - Tetrahedron Letters

AU - Overman, Lаrry E.

AU - Burk, R D

PY - 1984

DA - 1984/01/01

PB - Elsevier

SP - 5739-5742

IS - 50

VL - 25

SN - 0040-4039

SN - 1873-3581

ER -

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@article{1984_Overman,

author = {Lаrry E. Overman and R D Burk},

title = {The importance of vinylsilane stereochemistry and σ - π stabilization in iminium ion-vinylsilane cyclizations. A short total synthesis of the alkaloid (−) −epielwesine.},

journal = {Tetrahedron Letters},

year = {1984},

volume = {25},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016/S0040-4039(01)81674-9},

number = {50},

pages = {5739--5742},

doi = {10.1016/S0040-4039(01)81674-9}

}

MLA

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MLA Скопировать

Overman, Larry E., et al. “The importance of vinylsilane stereochemistry and σ - π stabilization in iminium ion-vinylsilane cyclizations. A short total synthesis of the alkaloid (−) −epielwesine..” Tetrahedron Letters, vol. 25, no. 50, Jan. 1984, pp. 5739-5742. https://doi.org/10.1016/S0040-4039(01)81674-9.

Издатель

Elsevier

Журнал

Tetrahedron Letters

scimago Q3

wos Q3

БС2

SJR

0.334

CiteScore

3.2

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)

Профили

Оверман Ларри Е