2002
DOI: 10.1070/mc2002v012n02abeh001566
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Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers

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Cited by 6 publications
(4 citation statements)
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“…The synthesis of compound 6 relies on the preparation of enantiomerically enriched carbocycles 7 and 8a , which we envisioned to be accessible in a short series of synthetic transformations. Specifically, cyclogeraniol acetate 21 was prepared in five steps following the reported literature procedures and subsequently analyzed to determine its enantiomeric excess by high-performance liquid chromatography (HPLC) analysis of the corresponding benzoyl ester (see the Supporting Information for details). Allylic oxidation of the exocyclic methyl group initially proved challenging.…”
Section: Resultsmentioning
confidence: 99%
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“…The synthesis of compound 6 relies on the preparation of enantiomerically enriched carbocycles 7 and 8a , which we envisioned to be accessible in a short series of synthetic transformations. Specifically, cyclogeraniol acetate 21 was prepared in five steps following the reported literature procedures and subsequently analyzed to determine its enantiomeric excess by high-performance liquid chromatography (HPLC) analysis of the corresponding benzoyl ester (see the Supporting Information for details). Allylic oxidation of the exocyclic methyl group initially proved challenging.…”
Section: Resultsmentioning
confidence: 99%
“…21 was prepared in three steps according to literature procedures and isolated as a colorless oil (7.4 g, 56% yield from 20 ). 1 H NMR (CDCl 3 , 500 MHz): δ 5.60 (s, 1H), 3.74 (s, 2H), 2.00 (s, 2H), 1.74 (s, 3H), 1.66–1.58 (m, 2H), 1.33 (s, 1H), 1.19 (dt, J = 8.7, 4.0 Hz, 1H), 1.02 (s, 3H), 0.89 (s, 3H). Enantiomeric excess (90% ee) was determined by chiral HPLC analysis of the corresponding benzoyl ester of cyclogeraniol 9 .…”
Section: Methodsmentioning
confidence: 99%
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“…Other enzymes were screened [26], and only the combined use of lipase from Candida antartica and vinyl propionate allowed the resolution of this isomer, although with modest enantioselectivity (E = 6.7). Similarly, the resolution of the sesquiterpenes drimenol (15) and albicanol (16), by means of this enzymatic approach, was extensively studied [27][28][29][30]. Moreover, in these cases, to achieve suitable enantioselectivity, specific acylation conditions were identified.…”
Section: Primary Alcoholsmentioning
confidence: 99%