{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,16]],"date-time":"2026-04-16T00:49:16Z","timestamp":1776300556981,"version":"3.50.1"},"reference-count":14,"publisher":"Elsevier BV","issue":"21","license":[{"start":{"date-parts":[[2000,5,1]],"date-time":"2000-05-01T00:00:00Z","timestamp":957139200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2000,5,1]],"date-time":"2000-05-01T00:00:00Z","timestamp":957139200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Tetrahedron Letters"],"published-print":{"date-parts":[[2000,5]]},"DOI":"10.1016\/s0040-4039(00)00594-3","type":"journal-article","created":{"date-parts":[[2002,7,25]],"date-time":"2002-07-25T09:57:26Z","timestamp":1027591046000},"page":"4123-4125","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":20,"title":["A short, efficient synthesis of the chiral auxiliary (+)-8-phenylneomenthol"],"prefix":"10.1016","volume":"41","author":[{"given":"Olga","family":"Caama\u00f1o","sequence":"first","affiliation":[]},{"given":"Franco","family":"Fern\u00e1ndez","sequence":"additional","affiliation":[]},{"given":"Xerardo","family":"Garc\u0131\u0301a-Mera","sequence":"additional","affiliation":[]},{"given":"Jos\u00e9 E","family":"Rodr\u0131\u0301guez-Borges","sequence":"additional","affiliation":[]}],"member":"78","reference":[{"key":"10.1016\/S0040-4039(00)00594-3_BIB1","doi-asserted-by":"crossref","unstructured":"Corey, E. J.; Becker, K. B.; Varma, R. K. J. Am. Chem. Soc. 1972, 94, 8616.","DOI":"10.1021\/ja00779a074"},{"key":"10.1016\/S0040-4039(00)00594-3_BIB2","doi-asserted-by":"crossref","unstructured":"Quinkert, G.; Schwalz, H. G.; Dzierzynski, E. M.; D\u00fcrner, G.; Bats, J. W. Angew. Chem., Int. Ed. Engl.. 1986, 25, 992.","DOI":"10.1002\/anie.198609921"},{"key":"10.1016\/S0040-4039(00)00594-3_BIB3","unstructured":"For use of (\u2212)-8-phenylmenthol 3 and (+)-8-phenylisomenthol 4 see Ref. 4 and 5, respectively"},{"key":"10.1016\/S0040-4039(00)00594-3_BIB4","unstructured":"(a) Oppolzer, W.; Robbiani, C.; Battig, K. Helv. Chim. Acta 1980, 63, 2015. (b) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989. (c) Binger, P.; Brinkmann, A.; Richter, W. J. Tetrahedron Lett. 1983, 24, 3599. (d) D'Angelo, J.; Maddaluno, J. J. Am. Chem. Soc. 1986, 108, 8112. (e) Solladie-Cavallo, A.; Benchegroun, M. Tetrahedron Asymm. 1991, 2, 1165. (f) Takagi, R.; Kimura, J.; Shinohara, Y.; Ohba, Y.; Takezono, K.; Hiraga, Y.; Kojima, S.; Okhata, K. J. Chem. Soc., Perkin-Trans 1 1998, 698. (g) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.; Rein, T. J. Org. Chem. 1998, 63, 8284. (h) Kubo, Y.; Yoshioka, M.; Nakajima, S.; Inamura, I. Tetrahedron Lett. 1999, 40, 2335. (i) Donohoe, T. J.; Guyo, P. M.; Helliwell, M. Tetrahedron Lett. 1999, 40, 435."},{"key":"10.1016\/S0040-4039(00)00594-3_BIB5","doi-asserted-by":"crossref","unstructured":"Whitesell, J. K.; Lin, C.-L.; Buchanan, C. M.; Chen, H.-H.; Minton, M. A. J. Org. Chem. 1986, 51, 551.","DOI":"10.1021\/jo00354a032"},{"key":"10.1016\/S0040-4039(00)00594-3_BIB6","doi-asserted-by":"crossref","unstructured":"Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 7908.","DOI":"10.1021\/ja00856a074"},{"key":"#cr-split#-10.1016\/S0040-4039(00)00594-3_BIB7.1","doi-asserted-by":"crossref","unstructured":"Vollhardt, P. C. Organometallics 1988, 7, 883. (b) Potin, D.","DOI":"10.1021\/om00094a015"},{"key":"#cr-split#-10.1016\/S0040-4039(00)00594-3_BIB7.2","doi-asserted-by":"crossref","unstructured":"Dumas, F. Synth. Commun. 1990, 20, 2805.","DOI":"10.1080\/00397919008051493"},{"key":"#cr-split#-10.1016\/S0040-4039(00)00594-3_BIB7.3","doi-asserted-by":"crossref","unstructured":"(a) Halterman, R. L.; Vollhardt, P. C. Organometallics 1988, 7, 883.","DOI":"10.1021\/om00094a015"},{"key":"#cr-split#-10.1016\/S0040-4039(00)00594-3_BIB7.4","doi-asserted-by":"crossref","unstructured":"(b) Potin, D.; Dumas, F. Synth. Commun. 1990, 20, 2805.","DOI":"10.1080\/00397919008051493"},{"key":"10.1016\/S0040-4039(00)00594-3_BIB8","unstructured":"(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanone 6: To a solution of pyridine (24.9 g, 311 mmol) in CH2Cl2 (260 mL) at 0\u00b0C were added, in small portions CrO3 (15.48 g, 155 mmol), then dropwise a solution of 3 (6 g, 25.8 mmol) in CH2Cl2 (25 mL). The resulting mixture was stirred for 45 min, filtered on Celite, the solids being washed with Et2O (4\u00d790 mL). The pooled organic extracts were concentrated to 50 mL, then washed with water (100 mL) and saturated brine (100 mL), and dried (Na2SO4). Evaporation of the solvents afforded an oil (6.4 g) which upon flash chromatography [silica gel 60 (210 g); hexane:AcOEt, 9:1] gave 6 as a colourless oil (5.7 g, 96%). [\u03b1]D23 \u221249 (c 1.0, CHCl3). IR (film) \u03bdmax: 1709 (CO) cm\u22121. 1H NMR (300 MHz, CDCl3): 0.97 (d, 3H, J=6 Hz, 5-CH3), 1.41 and 1.47 (2s, 6H, 8-(CH3)2), 1.50\u20131.89 (m, 5H), 1.91\u20132.06 (m, 1H, 6-H), 2.22\u20132.27 (m, 1H, 6-H), 2.61\u20132.70 (m, 1H, 2-H), 7.13\u20137.37 (m, 5Harom). 13C NMR (75 MHz, CDCl3): 22.73, 24.43, 26.91, 29.45, 35.09, 36.69, 39.43 (C-8), 52.76, 59.94, 125.91 (C-4\u2032), 126.16 (C-2\u2032+C-6\u2032), 128.38 (C-3\u2032+C-5\u2032), 150.31 (C-1\u2032), 211.92 (C-1)."},{"key":"10.1016\/S0040-4039(00)00594-3_BIB9","unstructured":"(1S,2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanol 2: A solution of 6 (8 g, 34.9 mmol) in THF (35 mL) was added dropwise to a 1.0 M solution of L-Selectride in THF (52 mL, 52 mmol) at 0\u00b0C, and the resulting mixture was stirred for 4 h at 0\u00b0C. Aqueous 3 M NaOH (11 mL, 33 mmol) was then added dropwise followed by slow addition of 30% H2O2 (18 mL, 180 mmol). After a further 30 min stirring at room temperature the mixture was extracted with Et2O (4\u00d730 mL), the combined organic phases being washed with water (2\u00d720 mL) and dried (Na2SO4). The solvents were removed in vacuo to leave an oil, which was purified by flash chromatography [silica gel 60 (220 g), hexane:AcOEt, 9:1] to afford 2 as a colourless oil (7.21 g, 89%). [\u03b1]D23 +34 (c 1.0, CHCl3). IR (film) \u03bdmax: 3464 (OH) cm\u22121. 1H NMR (300 MHz, CDCl3): 0.84 (d, 3H, J=6 Hz, 5-CH3), 0.88\u20131.11 (m, 2H), 1.38 and 1.40 (2s, 6H, 8-(CH3)2), 1.43\u20131.76 (m, 6H), 3.86 (virtual s, 1H, 1eq-H), 7.18 (td, 1H, J=7 Hz, 1 Hz, 4\u2032-H), 7.26\u20137.33 (m, 2H, 3\u2032-H+5\u2032-H), 7.37\u20137.40 (m, 2H, 2\u2032-H+6\u2032-H). 13C NMR (75 MHz, CDCl3): 21.75 (C-3), 22.63 (C-7), 26.26 (C-9), 26.53 (C-5), 28.05 (C-10), 36.06 (C-4), 40.60 (C-8), 44.26 (C-6), 52.71 (C-2), 68.62 (C-1), 125.92 (C-4\u2032), 126.59 (C-2\u2032+C-6\u2032), 128.42 (C-3\u2032+C-5\u2032), 150.31 (C-1\u2032)."},{"key":"10.1016\/S0040-4039(00)00594-3_BIB10","unstructured":"(1\u2032S,2\u2032S,5\u2032R)-5\u2032-Methyl-2\u2032-(1-methyl-1-phenylethyl)cyclohexyl 3,5-dinitrobenzoate 7: 3,5-Dinitrobenzoyl chloride (3.22 g; 14 mmol, freshly recrystallized from CCl4) was added at once to a solution of 2 (2.30 g, 10.37 mmol), anhydrous Et3N (1.98 mL, 14 mmol) and DMAP (20 mg) in anhydrous THF (200 mL) and the mixture was refluxed for 5 h with stirring, under an argon atmosphere. After cooling, the resulting mixture was concentrated to 20 mL, diluted with CH2Cl2 (80 mL) and washed with saturated NaHCO3 solution (3\u00d7100 mL) and saturated brine (100 mL). The organic layer was dried (Na2SO4), and the solvents were removed in vacuo to leave an oily residue, which was chromatographed [silica gel 60 (100 g), hexane:AcOEt, 9:1] affording 7 as a white solid (3.25 g, 77%). Mp 139\u2013140\u00b0C (Et2O-cyclohexane). [\u03b1]D23 +114 (c 1.0, CHCl3). IR (KBr) \u03bdmax: 1719 (CO) cm\u22121. 1H NMR (300 MHz, CDCl3): 0.83\u20130.86 (d, 3H, J=7 Hz, 5\u2032-CH3), 1.02\u20131.25 (m, 2H), 1.36 and 1.41 (2s, 6H, 8\u2032-(CH3)2), 1.58\u20131.99 (m, 6H), 5.45 (virtual s, 1H, 1\u2032eq-H), 6.91 (t, 1H, J=7 Hz, 4\u2032\u2032-H), 7.11 (t, 2H, J=8 Hz, 3\u2032\u2032-H+5\u2032-H), 7.24 (d, 2H, J=7 Hz, 2\u2032\u2032-H+6\u2032\u2032-H), 8.83 (d, 2H, J=2 Hz, 2-H+6-H), 9.18 (t, 1H, J=2 Hz, 4-H). 13C NMR (75 MHz, CDCl3): 22.29 (C-3\u2032), 23.26 (C-7\u2032), 26.30 (C-5\u2032), 27.51 (C-9\u2032), 27.88 (C-10\u2032), 35.65 (C-4\u2032), 40.19 (C-6\u2032), 40.34 (C-8\u2032), 52.19 (C-2\u2032), 74.27 (C-1\u2032), 122.47 (C-4), 125.76 (C-4\u2032\u2032), 126.63 (C-2\u2032\u2032+C-6\u2032\u2032), 128.40 (C-3\u2032\u2032+C-5\u2032\u2032), 129.52 (C-2+C-6), 134.80 (C-1), 148.40 (C-1\u2032\u2032), 148.87 (C-3+C-5), 161.71 (C(O))."},{"key":"10.1016\/S0040-4039(00)00594-3_BIB11","unstructured":"Results of this analysis will be published elsewhere."}],"container-title":["Tetrahedron Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403900005943?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403900005943?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,9,22]],"date-time":"2025-09-22T17:13:23Z","timestamp":1758561203000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0040403900005943"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2000,5]]},"references-count":14,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2000,5]]}},"alternative-id":["S0040403900005943"],"URL":"https:\/\/doi.org\/10.1016\/s0040-4039(00)00594-3","relation":{},"ISSN":["0040-4039"],"issn-type":[{"value":"0040-4039","type":"print"}],"subject":[],"published":{"date-parts":[[2000,5]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"A short, efficient synthesis of the chiral auxiliary (+)-8-phenylneomenthol","name":"articletitle","label":"Article Title"},{"value":"Tetrahedron Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/S0040-4039(00)00594-3","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"converted-article","name":"content_type","label":"Content Type"},{"value":"Copyright \u00a9 2000 Elsevier Science Ltd. All rights reserved.","name":"copyright","label":"Copyright"}]}}