2010
DOI: 10.1016/j.tetasy.2010.08.011
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Two-step, stereoselective synthesis of linalyl oxides by asymmetric allylic O-alkylation

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Cited by 11 publications
(12 citation statements)
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“…H NMR (500 MHz, CDCl 3 ) d 5.88 (dd, J = 17.3, 10.7 Hz, 1H), 5.19 (dd, J = 17.3, 1.5 Hz, 1H), 4.99 (dd, J = 10.6, 1.5 Hz, 1H), 3.80 (t, J = 7.2 Hz, 1H), 1.90 (ddd, J = 10.9, 8.3, 6.1 Hz, 1H), 1.83 (q, J = 7.3 Hz, 2H), 1.73 (ddd, J = 10.9, 8.3, 6.1 Hz, 1H), 1.32 (s, 3H), 1.23 (s, 3H), 1.13 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) d 143.85, 111.47, 85.70, 83.20, 71.27, 37.63, 27.39, 26.97, 26.46, 24.31.NMR data in accordance with literature [22]. Relevant NMR spectra and GC methods and traces can be found in the supporting information.…”
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confidence: 71%
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“…H NMR (500 MHz, CDCl 3 ) d 5.88 (dd, J = 17.3, 10.7 Hz, 1H), 5.19 (dd, J = 17.3, 1.5 Hz, 1H), 4.99 (dd, J = 10.6, 1.5 Hz, 1H), 3.80 (t, J = 7.2 Hz, 1H), 1.90 (ddd, J = 10.9, 8.3, 6.1 Hz, 1H), 1.83 (q, J = 7.3 Hz, 2H), 1.73 (ddd, J = 10.9, 8.3, 6.1 Hz, 1H), 1.32 (s, 3H), 1.23 (s, 3H), 1.13 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) d 143.85, 111.47, 85.70, 83.20, 71.27, 37.63, 27.39, 26.97, 26.46, 24.31.NMR data in accordance with literature [22]. Relevant NMR spectra and GC methods and traces can be found in the supporting information.…”
supporting
confidence: 71%
“…Conversion of rac-5 b with epoxide hydrolase preparations containing ADH [a] activity and product distribution. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 Due to unsatisfactory results with the iridiumbased catalyst, the strategy was altered to a Tsuji-Trost based approach, [22] in which biocatalysis could advan-tageously be combined with transition metal catalysis to obtain 11 stereoselectively (Scheme 5).…”
Section: Full Papermentioning
confidence: 99%
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“…Several syntheses have been published between 1981 and 2010 using a range of different strategies (e.g. enzymatic procedures, Sn- and Pd-catalyzed methods or even anodic oxidations) [131136]. In 2014 the Brown group proposed an auxiliary-controlled synthesis of trans -(+)-linalool oxide ( 79 ) using a permanganate-mediated type A oxidative cyclization as the key step (Scheme 16) [137].…”
Section: Reviewmentioning
confidence: 99%
“…The yield was very low, only 20.5%, and strict operation was requested. There are also many literature reports [14][15][16] , which used geraniol as the material, involving esterification, hydroxylation, and cyclization, to give the furanoid linalool oxide. In 1997, Nguefack et al [17] used nerol and geianiol as raw material respectively, involving Palladium(0)-catalysed synthesis of cis-and trans-linalool oxides.…”
Section: Introductionmentioning
confidence: 99%