Stereocontrolled preparation of cis- and rans-2,6-dialkylpiperidines via diastereoselective reaction of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives with Grignard reagents
Тип публикации: Journal Article
Дата публикации: 1998-11-01
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
We report here the syntheses of cis - and trans -2,6-disubstituted piperidines using chiral 1-aza-4-oxabicyclo[4.3.0]nonane synthon 1 , which shows high reactivity toward nucleophilic attack at its C-5 position. Bicyclic compounds resembling synthon 1 were transformed to cis - and trans -2,6-disubstituted piperidine derivatives via reactions with various Grignard reagents in a stereospecific manner. Using this methodology, (+)-solenopsin A ( 2b ) and both enantiomers of isosolenopsin A ( 3a and 3b ) were synthesized in an enantioselective manner from a single enantiomeric source.
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Poerwono H. et al. Stereocontrolled preparation of cis- and rans-2,6-dialkylpiperidines via diastereoselective reaction of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives with Grignard reagents // Tetrahedron. 1998. Vol. 54. No. 46. pp. 13955-13970.
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Poerwono H., Higashiyama K., Yamauchi T., Kubo H., OHMIYA S., Takahashi H. Stereocontrolled preparation of cis- and rans-2,6-dialkylpiperidines via diastereoselective reaction of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives with Grignard reagents // Tetrahedron. 1998. Vol. 54. No. 46. pp. 13955-13970.
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TY - JOUR
DO - 10.1016/S0040-4020(98)00863-1
UR - https://doi.org/10.1016/S0040-4020(98)00863-1
TI - Stereocontrolled preparation of cis- and rans-2,6-dialkylpiperidines via diastereoselective reaction of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives with Grignard reagents
T2 - Tetrahedron
AU - Poerwono, Hadi
AU - Higashiyama, Kimio
AU - Yamauchi, Takayasu
AU - Kubo, Hajime
AU - OHMIYA, Shigeru
AU - Takahashi, Hiroshi
PY - 1998
DA - 1998/11/01
PB - Elsevier
SP - 13955-13970
IS - 46
VL - 54
SN - 0040-4020
SN - 1464-5416
ER -
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@article{1998_Poerwono,
author = {Hadi Poerwono and Kimio Higashiyama and Takayasu Yamauchi and Hajime Kubo and Shigeru OHMIYA and Hiroshi Takahashi},
title = {Stereocontrolled preparation of cis- and rans-2,6-dialkylpiperidines via diastereoselective reaction of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives with Grignard reagents},
journal = {Tetrahedron},
year = {1998},
volume = {54},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/S0040-4020(98)00863-1},
number = {46},
pages = {13955--13970},
doi = {10.1016/S0040-4020(98)00863-1}
}
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Poerwono, Hadi, et al. “Stereocontrolled preparation of cis- and rans-2,6-dialkylpiperidines via diastereoselective reaction of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives with Grignard reagents.” Tetrahedron, vol. 54, no. 46, Nov. 1998, pp. 13955-13970. https://doi.org/10.1016/S0040-4020(98)00863-1.