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The stereochemistry of the major diastereoisomer was assigned on the basis of literature precedent for the oxidative cyclization of closely related substrates (see ref 10f,i).
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Commemorative Issue in Honor of Prof. B. S. Thyagarajan, ms. BT-336D (http://www.Arkat-usa.org/ark/journal/Volume2/Part3/Thyagarajan/BT-335D/336d. pdf).
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Cecil, A. R. L.; Brown, R. C. D. Arkivoc 2001, Part (xi) Commemorative Issue in Honor of Prof. B. S. Thyagarajan, ms. BT-336D (http://www.Arkat-usa.org/ark/journal/Volume2/Part3/Thyagarajan/BT-335D/336d. pdf).
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(2001)
Arkivoc
, Issue.PART XI
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Cecil, A.R.L.1
Brown, R.C.D.2
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76
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0035803638
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Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496-4498.
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(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 4496-4498
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Brown, R.C.D.1
Keily, J.F.2
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77
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2442639282
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note
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major signals, leading us to initially report a higher value of 10:1. The dr value of 6:1 was confirmed from the isolated yields of 5 and 16.
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78
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2442686980
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note
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The diastereofacial selectivity observed for the oxidative cyclization of enantiomerically enriched N-enoyl oxazolidinones was previously explained by dipolar organization of the substrate (see ref 10f).
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79
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0012321996
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Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim
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Reiser, O. In Organic Synthesis Highlights IV; Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim, 2000; pp 11-16.
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(2000)
Organic Synthesis Highlights IV
, pp. 11-16
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Reiser, O.1
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80
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2442658121
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note
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13C NMR spectra.
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82
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2442716668
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note
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3).
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83
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0343632337
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It has previously been observed that the optical rotation value of acetogenins is largely due to the stereochemistry of the butenolide, and to a lesser extent due to the stereochemistry of the THF diol portion: Duret, P.; Figadère, B.; Hocquemiller, R.; Cavé, A. Tetrahedron Lett. 1997, 38, 8849-8852.
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(1997)
Tetrahedron Lett.
, vol.38
, pp. 8849-8852
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Duret, P.1
Figadère, B.2
Hocquemiller, R.3
Cavé, A.4
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84
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2442665611
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note
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Each of the four isomers (1, ent-1, 2, and ent-2) gave a separate and single peak on a Chiral CD-Ph HPLC column, eluting with i-PrOH/hexane (15:85). Retention times: 1 (14.5 min), 2 (17.3 min), ent-1 (18.7 min), ent-2 (15.7 min). See the Supporting Information for an HPLC trace for a mixed sample of 1 and 2.
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