Synthesis of enantiopure cis- and trans-2-aminocyclohexane-1-carboxylic acids from octahydroquinazolin-4-ones

[Display omitted] The chemoselective and diastereoselective hydrogenation of 2,3-dihydro-3-[( S)-α-methylbenzyl]-4-quinazolinone 2 affords octahydroquinazolinones cis- 3 and cis- 4. Epimerization of cis- 3 and cis- 4 using t-BuO −K + produces trans- 5 and trans- 6, respectively. Hydrolysis with HCl...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2004-11, Vol.15 (22), p.3545-3549
Main Authors: Priego, Jaime, Flores, Patricia, Ortiz-Nava, Claudia, Escalante, Jaime
Format: Article
Language:English
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Summary:[Display omitted] The chemoselective and diastereoselective hydrogenation of 2,3-dihydro-3-[( S)-α-methylbenzyl]-4-quinazolinone 2 affords octahydroquinazolinones cis- 3 and cis- 4. Epimerization of cis- 3 and cis- 4 using t-BuO −K + produces trans- 5 and trans- 6, respectively. Hydrolysis with HCl of these octahydroquinazolinones leads to the free, enantiomerically pure, cis- and trans-2-aminocyclohexane-1-carboxylic acids 7– 10.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2004.08.032