{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,9,23]],"date-time":"2025-09-23T13:06:36Z","timestamp":1758632796941},"reference-count":9,"publisher":"Elsevier BV","issue":"31","license":[{"start":{"date-parts":[[2001,7,1]],"date-time":"2001-07-01T00:00:00Z","timestamp":993945600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Tetrahedron Letters"],"published-print":{"date-parts":[[2001,7]]},"DOI":"10.1016\/s0040-4039(01)01000-0","type":"journal-article","created":{"date-parts":[[2003,3,25]],"date-time":"2003-03-25T20:16:11Z","timestamp":1048623371000},"page":"5239-5240","source":"Crossref","is-referenced-by-count":8,"title":["A new, convenient synthesis of the chiral auxiliary (+)-8-phenylisomenthol"],"prefix":"10.1016","volume":"42","author":[{"given":"Franco","family":"Fern\u00e1ndez","sequence":"first","affiliation":[]},{"given":"Xerardo","family":"Garc\u0131\u0301a-Mera","sequence":"additional","affiliation":[]},{"given":"Jos\u00e9","family":"Enrique Rodr\u0131\u0301guez-Borges","sequence":"additional","affiliation":[]},{"given":"Jos\u00e9","family":"Manuel Blanco","sequence":"additional","affiliation":[]}],"member":"78","reference":[{"key":"10.1016\/S0040-4039(01)01000-0_BIB1","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1055\/s-1995-3957","author":"Jones","year":"1995","journal-title":"Synthesis"},{"key":"10.1016\/S0040-4039(01)01000-0_BIB2","doi-asserted-by":"crossref","first-page":"203","DOI":"10.15227\/orgsyn.065.0203","volume":"65","author":"Ort","year":"1987","journal-title":"Org. Synth."},{"key":"10.1016\/S0040-4039(01)01000-0_BIB3","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1021\/jo00354a032","volume":"51","author":"Whitesell","year":"1986","journal-title":"J. Org. Chem."},{"key":"10.1016\/S0040-4039(01)01000-0_BIB5","unstructured":"Rodr\u0131\u0301guez-Borges, J. E. Ph.D. Dissertation, Universidade de Santiago de Compostela, 1995"},{"key":"10.1016\/S0040-4039(01)01000-0_BIB6","doi-asserted-by":"crossref","first-page":"5663","DOI":"10.1016\/S0040-4039(98)01102-2","volume":"39","author":"Blanco","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(01)01000-0_BIB7","doi-asserted-by":"crossref","first-page":"4805","DOI":"10.1016\/S0957-4166(00)00454-7","volume":"11","author":"Fern\u00e1ndez","year":"2000","journal-title":"Tetrahedron: Asymmetry"},{"key":"10.1016\/S0040-4039(01)01000-0_BIB9","unstructured":"(3R,6S)-3-Methyl-6-(1-methyl-1-phenylethyl)-1-cyclohexene, 5: Compound 4 (1.1 g, 3.79 mmol) was heated for 1 h at 200\u00b0C (without any solvent). The residue was purified by flash chromatography [silica gel 60; hexane] affording 5 as an oil (0.73 g; 90%). [\u03b1]D23 +71.5 (c 1.0, CHCl3). IR (film) \u03bdmax: 3019, 2958, 2867, 1559, 1495, 1457, 1365, 1311, 1240, 1098, 1030, 961, 765 cm\u22121. 1H NMR (300 MHz, CDCl3): 0.95 (d, 3H, J=7.1 Hz, 3-CH3), 1.29 and 1.31 (2s, 6H, C-(CH3)2), 1.33\u20131.42 (m, 3H), 1.61\u20131.66 (m, 1H), 2.14\u20132.15 (m, 1H), 2.38\u20132.40 (m, 1H), 5.47 (d\u00d7t, 1H, Jd=10.3 Hz, Jt=1.7 Hz, 2-H), 5.66 (d\u00d7t, 1H, Jd=10.3 Hz, Jt=3.2 Hz, 1-H), 7.17\u20137.22 (m, 1H, ArH), 7.26\u20137.39 (m, 4H, ArH). 13C NMR (75 MHz, CDCl3): 20.65 (CH3), 21.36 (CH2), 25.60 (CH3), 25.77 (CH3), 29.13 (CH), 29.65 (CH2), 40.64 (C-8), 46.70 (CH), 125.83 (C-4\u2032), 126.54 and 126.61 (C-2\u2032+C-6\u2032), 128.30 and 128.35 (C-3\u2032+C-5\u2032), 134.75 (C-1+C-2), 150.17 (C-1\u2032)."},{"key":"10.1016\/S0040-4039(01)01000-0_BIB10","unstructured":"(1R,2S,3R,6R)-1,2-Epoxy-3-methyl-6-(1-methyl-1-phenylethyl)cyclohexane, 6: A solution of 5 (0.59 g, 2.75 mmol) in dry Cl2CH2 (4 mL) was added dropwise under argon to a solution of 70% m-CPBA (0.85 g, 3.40 mmol) in dry Cl2CH2 (10 mL) at 0\u00b0C. After stirring for 3 h at room temperature the mixture was treated with a saturated aqueous solution of NaSO3H (80 mL) and extracted with Cl2CH2 (3\u00d780 mL). The combined organic phases were washed with saturated K2CO3 (3\u00d790 mL) and brine (80 mL), and after drying (Na2SO4) the solvents were removed in vacuo, affording 6 as a colourless oil (0.59 g; 93%). [\u03b1]D23 +30.2 (c 1.0, CHCl3). IR (film) \u03bdmax: 3057, 2962, 1598, 1496, 1444, 1369, 1128, 1032, 930, 800, 765 cm\u22121. 1H NMR (300 MHz, CDCl3): 1.00 (d, 3H, J=7.2 Hz, 3-CH3), 1.03\u20131.27 (m, 3H), 1.33 and 1.41 (2s, 6H, C-(CH3)2), 1.54\u20131.63 (m, 1H), 2.14\u20132.27 (m, 2H, 3-H and 6-H), 2.79\u20132.87 (m, 2H, 1-H and 2-H), 7.16\u20137.22 (m, 1H, ArH), 7.29\u20137.41 (m, 4H, ArH). 13C NMR (75 MHz, CDCl3): 15.80 (CH3), 17.31 (CH2), 24.74 (CH2), 25.53 (CH3), 26.27 (CH3), 27.23 (CH), 40.60 (C-8), 44.71 (CH), 54.36 (CH), 58.19 (CH), 126.19 (C-4\u2032), 126.49 (C-2\u2032+C-6\u2032), 128.60 (C-3\u2032+C-5\u2032), 149.16 (C-1\u2032)."},{"key":"10.1016\/S0040-4039(01)01000-0_BIB11","unstructured":"(1S,2R,5R)-2-(1-Methyl-1-phenylethyl)-5-methylcyclohexanol, 1: A 1.0 M solution of lithium triethylborohydride in dry THF (4.3 mL, 10 equiv.) was added under argon, at room temperature and in one dose, to a solution of 6 (100 mg, 0.43 mmol) in 5 mL of the same solvent. The mixture was cooled to 0\u00b0C, treated with 50 mL of 5% NaOH solution followed by 25 mL of 3% H2O2, and extracted with Et2O (3\u00d750 mL). The combined organic phases were washed with brine (80 mL), and after drying (Na2SO4) the solvents were removed in vacuo, leaving an oil that upon purification by flash chromatography [silica gel 60; 9:1 hexane\/Et2O] afforded 1 as a colourless oil (98 mg; 98%). [\u03b1]D23 +11.5 (c 1.0, CHCl3). IR (film) \u03bdmax: 3566, 3402, 3087, 3057, 2921, 1601, 1495, 1444, 1380, 1343, 1155, 1061, 1031, 1014, 972, 763, 700 cm\u22121. 1H NMR (CDCl3): 0.93 (d, 3H, J=7.2 Hz, 5-CH3), 1.31 and 1.43 (2s, 6H, C-(CH3)2), 1.20\u20131.55 (m, 5H), 1.61\u20131.77 (m, 2H), 1.97\u20132.05 (m, 1H), 3.76 (d\u00d7t, Jt=9.7 Hz, Jd=4.3 Hz, 1ax-H), 7.15\u20137.21 (m, 1H, 4\u2032-H), 7.29\u20137.34 (m, 2H, 3\u2032-H+5\u2032-H), 7.38\u20137.41 (m, 2H, 2\u2032-H+6\u2032-H). 13C NMR (CDCl3): 19.08 (CH3), 21.65 (CH2), 24.91 (CH3), 28.06 (CH), 28.83 (CH3), 31.88 (CH2), 40.30 (C-8), 42.24 (CH2), 55.39 (CH), 69.18 (C-1), 126.18 (C-4\u2032+C-2\u2032+C-6\u2032), 128.80 (C-3\u2032+C-5\u2032), 150.70 (C-1\u2032)."}],"container-title":["Tetrahedron Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403901010000?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403901010000?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2019,4,25]],"date-time":"2019-04-25T19:21:19Z","timestamp":1556220079000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0040403901010000"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2001,7]]},"references-count":9,"journal-issue":{"issue":"31","published-print":{"date-parts":[[2001,7]]}},"alternative-id":["S0040403901010000"],"URL":"https:\/\/doi.org\/10.1016\/s0040-4039(01)01000-0","relation":{},"ISSN":["0040-4039"],"issn-type":[{"value":"0040-4039","type":"print"}],"subject":[],"published":{"date-parts":[[2001,7]]}}}