Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 8. Synthesis and ring opening reactions of cis- and trans- oxides derived from 3-benzyloxycyclohexene and 2-benzyloxy-5,6-dihydro-2H-pyran
Publication type: Journal Article
Publication date: 1994-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The regiochemical outcome of the ring opening of 1,2-epoxides bearing polar remote functionalization through chelation processes assisted by metal ions, was verified in cyclic oxirane systems having the polar functionality in an allylic position to the oxirane ring. The diastereoisomeric cis/trans epoxide pairs 5,6 and 7,8 derived from 3-benzyloxycyclohexene, and 2-benzyloxy-5,6-dihydro-2H-pyran, respectively, were prepared and several of their opening reactions were studied. The regioselectivity observed largely depends on the reaction conditions (standard or metal-assisted) and, interestingly, on the nature of the nucleophile used.
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Calvani F. et al. Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 8. Synthesis and ring opening reactions of cis- and trans- oxides derived from 3-benzyloxycyclohexene and 2-benzyloxy-5,6-dihydro-2H-pyran // Tetrahedron. 1994. Vol. 50. No. 45. pp. 12999-13022.
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Calvani F., Crotti P., Gardelli C., Pineschi M. Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 8. Synthesis and ring opening reactions of cis- and trans- oxides derived from 3-benzyloxycyclohexene and 2-benzyloxy-5,6-dihydro-2H-pyran // Tetrahedron. 1994. Vol. 50. No. 45. pp. 12999-13022.
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TY - JOUR
DO - 10.1016/S0040-4020(01)81219-9
UR - https://doi.org/10.1016/S0040-4020(01)81219-9
TI - Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 8. Synthesis and ring opening reactions of cis- and trans- oxides derived from 3-benzyloxycyclohexene and 2-benzyloxy-5,6-dihydro-2H-pyran
T2 - Tetrahedron
AU - Calvani, Federico
AU - Crotti, Paolo
AU - Gardelli, Cristina
AU - Pineschi, Mauro
PY - 1994
DA - 1994/01/01
PB - Elsevier
SP - 12999-13022
IS - 45
VL - 50
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{1994_Calvani,
author = {Federico Calvani and Paolo Crotti and Cristina Gardelli and Mauro Pineschi},
title = {Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 8. Synthesis and ring opening reactions of cis- and trans- oxides derived from 3-benzyloxycyclohexene and 2-benzyloxy-5,6-dihydro-2H-pyran},
journal = {Tetrahedron},
year = {1994},
volume = {50},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0040-4020(01)81219-9},
number = {45},
pages = {12999--13022},
doi = {10.1016/S0040-4020(01)81219-9}
}
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MLA
Copy
Calvani, Federico, et al. “Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 8. Synthesis and ring opening reactions of cis- and trans- oxides derived from 3-benzyloxycyclohexene and 2-benzyloxy-5,6-dihydro-2H-pyran.” Tetrahedron, vol. 50, no. 45, Jan. 1994, pp. 12999-13022. https://doi.org/10.1016/S0040-4020(01)81219-9.