Stereocomplementary desymmetrizations of divinylcarbinols by zirconium(IV)- vs. titanium(IV)-mediated asymmetric epoxidations

Advanced Synthesis and Catalysis

Volumn 350, Issue 7-8, 2008, Pages 1131-1148

  Kramer, Rainer ^a   Berkenbusch, Thilo ^b   Brückner, Reinhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

Author keywords

Diastereoselectivity; Enantioselectivity; Epoxy alcohols; Kinetic resolution; Sharpless asymmetric epoxidation

Indexed keywords

EID: 53849092068     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700608     Document Type: Article

References (68)

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49. This precedent is compared with our results in the concluding section of this paper.
50. 4,OH ≈ 7.5, 4-H (20)].
51. R = 54.0 min for ent-syn-12.
52. 1H NMR signal of the minor diastereomer could not be detected.
53. R = 15.1 min for anti-13.
54. R = 27.8 min for ent-syn-13.
55. 3,2 = 2.3 Hz, 3-H (anti-14)].
56. R = 58.1 min for ent-anti-14.
57. 1H NMR spectra.
58. R = 28.8 min for syn-14.
59. trans-oxirane 3.0 Hz according to: E. Pretsch, H. Seibl, W. Simon, Tabellen zur Strukturaufklärung organischer Verbindungen mit spektroskopischen Methoden, 3rd edn., Springer Verlag, Berlin 1990, H65.
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61. 2 [(2S,4R)-25]}.
62. δ = 142.24) for syn-25..
63. The absolute configurations mentioned in this paragraph and drawn in Scheme 8 and Scheme 9 were not yet known at this point of our investigation.
64. 3)} by same procedure (47% yield).
65. 4Si as internal standard) due to insufficiently separated signals ⇒ 1,3-diol:1,2-diol ≥ 79:21).
66. a) R. Kramer, Dissertation, Universität Freiburg, 2007;
67. b) R. Kramer, R. Brückner, manuscript in preparation.
68. [2] cf. also p. 721 in D. C. Dittmer, R. P. Discordia, Y. Zhang, C. K. Murphy, A. Kumar, A. S. Pepito, Y. Wang, J. Org. Chem. 1993, 58, 718-731.