Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid Esters
Studies on the use of lactonization in the asymmetric synthesis of 6,6-dimethyl-4-isopropyl-3-oxabicyclo[3.1.0]hexan-2-one were described. An asymmetrically induced lactonization reaction was performed on 3,3,6-trimethyl-4(E)-heptenoic acid esters (1) and enantiomerically pure alcohols such as (−)-m...
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| Language: | English |
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Wiley
2018-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2018/6135281 |
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| author | Robert Obara Jacek Łyczko Antoni Szumny |
| author_facet | Robert Obara Jacek Łyczko Antoni Szumny |
| author_sort | Robert Obara |
| collection | DOAJ |
| description | Studies on the use of lactonization in the asymmetric synthesis of 6,6-dimethyl-4-isopropyl-3-oxabicyclo[3.1.0]hexan-2-one were described. An asymmetrically induced lactonization reaction was performed on 3,3,6-trimethyl-4(E)-heptenoic acid esters (1) and enantiomerically pure alcohols such as (−)-menthol (a), (+)-menthol (b), (−)-borneol (c), (+)-isomenthol (d), (−)-isopinocampheol (e), and (S)-(−)-1-(2-bornylphenyl)-1-ethanol (f). The enantiomerically pure alcohols that were used as ancillary chiral substances were characterized by markedly different values of induction power; menthol (a, b), borneol (c), and phenetyl alcohol (f) performed better in asymmetric δ-lactonization, whereas isomenthol (d) and isopinocampheol (e) tended to favor asymmetric γ-lactonization. |
| format | Article |
| id | doaj-art-724ab70b05624a97a8dd92dfcb8ff389 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2018-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-724ab70b05624a97a8dd92dfcb8ff3892025-08-20T03:33:42ZengWileyJournal of Chemistry2090-90632090-90712018-01-01201810.1155/2018/61352816135281Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid EstersRobert Obara0Jacek Łyczko1Antoni Szumny2Institute of Chemistry, Jan Kochanowski University, Świętokrzyska 15G, 25-406 Kielce, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandStudies on the use of lactonization in the asymmetric synthesis of 6,6-dimethyl-4-isopropyl-3-oxabicyclo[3.1.0]hexan-2-one were described. An asymmetrically induced lactonization reaction was performed on 3,3,6-trimethyl-4(E)-heptenoic acid esters (1) and enantiomerically pure alcohols such as (−)-menthol (a), (+)-menthol (b), (−)-borneol (c), (+)-isomenthol (d), (−)-isopinocampheol (e), and (S)-(−)-1-(2-bornylphenyl)-1-ethanol (f). The enantiomerically pure alcohols that were used as ancillary chiral substances were characterized by markedly different values of induction power; menthol (a, b), borneol (c), and phenetyl alcohol (f) performed better in asymmetric δ-lactonization, whereas isomenthol (d) and isopinocampheol (e) tended to favor asymmetric γ-lactonization.http://dx.doi.org/10.1155/2018/6135281 |
| spellingShingle | Robert Obara Jacek Łyczko Antoni Szumny Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid Esters Journal of Chemistry |
| title | Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid Esters |
| title_full | Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid Esters |
| title_fullStr | Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid Esters |
| title_full_unstemmed | Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid Esters |
| title_short | Enantioselective Lactonization of 3,3,6-Trimethyl-4(E)-heptenoic Acid Esters |
| title_sort | enantioselective lactonization of 3 3 6 trimethyl 4 e heptenoic acid esters |
| url | http://dx.doi.org/10.1155/2018/6135281 |
| work_keys_str_mv | AT robertobara enantioselectivelactonizationof336trimethyl4eheptenoicacidesters AT jacekłyczko enantioselectivelactonizationof336trimethyl4eheptenoicacidesters AT antoniszumny enantioselectivelactonizationof336trimethyl4eheptenoicacidesters |