Enantioselective Synthesis and X Ray determination of (+)((4aS,5S,8aS)-5,8a-dimethyl-7-methyleneoctahydro-2H-spiro [naphthalene-1,2'-[1,3]dioxolan]-5-yl)methyl-4-iodobenzoate
| Autor: | Leonelli F., Trombetta A., La Bella A., Lucarelli G., Demitri N., Lamba D., Migneco L.M., Marini Bettolo R. |
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| Jazyk: | angličtina |
| Rok vydání: | 2019 |
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| Zdroj: | European journal of organic chemistry 2019 (2019): 1594–1599. doi:10.1002/ejoc.201801771 info:cnr-pdr/source/autori:Leonelli F., Trombetta A., La Bella A., Lucarelli G., Demitri N., Lamba D., Migneco L.M., Marini Bettolo R./titolo:Enantioselective Synthesis and X Ray determination of (+)((4aS,5S,8aS)-5,8a-dimethyl-7-methyleneoctahydro-2H-spiro [naphthalene-1,2'-[1,3]dioxolan]-5-yl)methyl-4-iodobenzoate/doi:10.1002%2Fejoc.201801771/rivista:European journal of organic chemistry (Print)/anno:2019/pagina_da:1594/pagina_a:1599/intervallo_pagine:1594–1599/volume:2019 |
| Popis: | The D and L amino acid mediated enantioselective intramolecular aldol reaction of 4-((1-methyl-2,6-dioxo-cyclohexyl)methyl)-pent-4-enal 1 leading, after dehydration, to (-)-(R) and (+)-(S) 4a-methyl-3-methylene-5-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalene-1-carbaldehyde 2 was explored. It was found that (-)-(R) carbaldehyde 2 is enantioselectively formed in the presence of l-amino acids while (+)-(S) carbaldehyde 2 is enantioselectively formed in the presence of d-amino acids. (-)-(R) Carbaldehyde 2 was then transformed into (+)-22. The absolute configuration and relative stereochemistry of the latter was established by single-crystal X-ray diffraction analysis of p-iodobenzoate (+)-23. |
| Databáze: | OpenAIRE |
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