The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo[3.2.1]oct-6-en-2-one to soft electrophiles.
Publication type: Journal Article
Publication date: 1993-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Nitrosation of 7-oxabicyclo[2.2.1]hept-5-en-2-exo-ylmethyl amine (20) gave 7-oxabicyclo[2.2.1]hept-5-en-2-exo-methanol (22) whereas 7-oxabicyclo[2.2.1]hept-5-en-2-endo-ylmethylamine (21) afforded a 1:1 mixture of 8-oxabicyclo[3.2.1]oct-6-en-2-ols (23) and 8-oxabicyclo[3.2.1]oct-3-en-2-ols (24). Nitrosations of 2-exo- (28) and 2-endo-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ol (29) gave mixtures of 8-oxabicyclo[3.2.1]oct-6-en-2-one (25) and 8-oxabicyclo[3.2.1]oct-6-en-3-one (37). The preference for the C(3) methylene group migration giving 25 was the best (12:1) in the case of the 2-endo-aminomethyl alcohol 29. Compared with the nitrosations of bicyclo[2.2.1]heptane analogues, the 7-oxa bridge in 28 and 29 enhances the preference for the C(3) methylene group migration vs. the C(1) methine group migration. The Tiffeneau-Demjanov one-carbon ring enlargement reactions of 2-exo-aminomethyl-7-oxabicyclo[2.2.1]heptan-2-endo-ol (30). 2-exo-aminomethyl-5-chloro (32) and 2-exo-amino-methyl-6-chloro-7-oxabicyclo[2.2.1]hept-5-en-2-endo-ol (33) are also reported. Under kinetically controlled conditions, 8-oxabicyclo[3.2.1]oct-6-en-2-one (25) adds to electrophiles EX=PhSeCl. PhSeBr, 2,4-(NO)2C6H3SCl with high stereo- and regioselectivity giving the corresponding 8-oxabicyclo[3.2.1]-octan-2-ones where E substitutes the exo position of C(6) and X the endo position of C(7).
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Fattori D., Henry S., Vogel P. The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo[3.2.1]oct-6-en-2-one to soft electrophiles. // Tetrahedron. 1993. Vol. 49. No. 8. pp. 1649-1664.
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Fattori D., Henry S., Vogel P. The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo[3.2.1]oct-6-en-2-one to soft electrophiles. // Tetrahedron. 1993. Vol. 49. No. 8. pp. 1649-1664.
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TY - JOUR
DO - 10.1016/S0040-4020(01)80352-5
UR - https://doi.org/10.1016/S0040-4020(01)80352-5
TI - The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo[3.2.1]oct-6-en-2-one to soft electrophiles.
T2 - Tetrahedron
AU - Fattori, Daniela
AU - Henry, Sylvie
AU - Vogel, P.
PY - 1993
DA - 1993/01/01
PB - Elsevier
SP - 1649-1664
IS - 8
VL - 49
SN - 0040-4020
SN - 1464-5416
ER -
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@article{1993_Fattori,
author = {Daniela Fattori and Sylvie Henry and P. Vogel},
title = {The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo[3.2.1]oct-6-en-2-one to soft electrophiles.},
journal = {Tetrahedron},
year = {1993},
volume = {49},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0040-4020(01)80352-5},
number = {8},
pages = {1649--1664},
doi = {10.1016/S0040-4020(01)80352-5}
}
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MLA
Copy
Fattori, Daniela, et al. “The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo[3.2.1]oct-6-en-2-one to soft electrophiles..” Tetrahedron, vol. 49, no. 8, Jan. 1993, pp. 1649-1664. https://doi.org/10.1016/S0040-4020(01)80352-5.