Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems
Тип публикации: Journal Article
Дата публикации: 1997-03-01
scimago Q3
wos Q3
БС2
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
Ortho lithiated protected anilines and phenols undergo exclusive addition to fenchone from the exo face. The corresponding adducts, under acidic conditions undergo cationic rearrangement followed by internal trapping of the new cation with amino, hydroxyl or methoxyl substituents to give enantiomerically pure chiral heterocyclic ring systems. The nature of the rearrangement is dependent on the donor group and its ability to stabilise a positive charge. With an amino donor group a product due to Wagner-Meerwein rearrangement is formed while with a methoxy donor group Nametkin rearrangement is the preferred pathway.
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Starling S. M., Vonwiller S. C. Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems // Tetrahedron Letters. 1997. Vol. 38. No. 12. pp. 2159-2162.
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Starling S. M., Vonwiller S. C. Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems // Tetrahedron Letters. 1997. Vol. 38. No. 12. pp. 2159-2162.
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TY - JOUR
DO - 10.1016/S0040-4039(97)00271-2
UR - https://doi.org/10.1016/S0040-4039(97)00271-2
TI - Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems
T2 - Tetrahedron Letters
AU - Starling, Scott M
AU - Vonwiller, Simone C.
PY - 1997
DA - 1997/03/01
PB - Elsevier
SP - 2159-2162
IS - 12
VL - 38
SN - 0040-4039
SN - 1873-3581
ER -
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@article{1997_Starling,
author = {Scott M Starling and Simone C. Vonwiller},
title = {Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems},
journal = {Tetrahedron Letters},
year = {1997},
volume = {38},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/S0040-4039(97)00271-2},
number = {12},
pages = {2159--2162},
doi = {10.1016/S0040-4039(97)00271-2}
}
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MLA
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Starling, Scott M., and Simone C. Vonwiller. “Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems.” Tetrahedron Letters, vol. 38, no. 12, Mar. 1997, pp. 2159-2162. https://doi.org/10.1016/S0040-4039(97)00271-2.