Regioselective cis,vic-dihydroxylation of α,β,γ,δ- unsaturated carboxylic esters: Enhanced γ,δ-selectivity by employing trifluoroethyl or hexafluoroisopropyl esters

Synlett

Volumn , Issue 16, 2006, Pages 2641-2645

  Schmidt Leithoff, Joachim ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

, , , unsaturated esters; Asymmetric dihydroxylation; Hexafluoroisopropyl ester; Regioselectivity; Trifluoroethyl esters

Indexed keywords

ALDEHYDE DERIVATIVE; ESTER DERIVATIVE; FLUORINE; HEXAFLUOROISOPROPYL ESTER; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; TRIFLUOROETHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIHYDROXYLATION; FLUORINATION; OLEFINATION; SYNTHESIS;

EID: 33750071740     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951473     Document Type: Article

References (45)

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23. 2PHAL. The reason is that Sharpless et al. (ref. 3) found decreased γ,δ:α,β dihydroxylation ratios employing AD-mix β instead of AD-mix α for the dihydroxylation of α,β,γ,δ-unsaturated esters 1 (→ 2:iso-2 = 83:17 instead of 87:13) or 3 (→ 4:iso-4 = 56:44 instead of 60:40).
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31. 4: Schmidt-Leithoff J.; Ph.D. Dissertation; Universität Freiburg, 2006.
32. 3 (see Scheme 1). This might be due to our catalyst/ligand ratio being 1:5 and Sharpless' being 1:1 and 1:2, respectively.
33. 2: 362.0741; found: 362.0735.
34. 7O: 131.0497; found: 131.0495.
35. 17 It was obtained in 96% yield by a carbodiimide-mediated esterification of hexafluoroisopropanol with the carboxylic acid obtained from the saponification of ethyl ester 29.
36. 21
37. Morphy, J. R.; Rankovic, Z.; York, M. Tetrahedron 2003, 59, 2137.
38. 2 and then with trifluoro-ethanol (Σ = 58%): Birnbaum, J. C.; Busche, B.; Lin, Y.; Shaw, W. J.; Fryxell, G. E. Chem. Commun. 2002, 1374.
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40. 23 but used en route to allenic carboxylic esters and not in a Wittig reaction.
41. 4 bond.
42. 2),
43. 2: 294.0868; found: 294.0867.
44. 4P: 165.0317; found: 165.0316.
45. Compound 40 was obtained in 78% yield by esterification of 2-bromopropionic acid. A two-step synthesis of 40 via acid chloride formation from 2-bromopropionic acid followed by trifluoroethanolysis yielded 83% of 40: Aggarwal, V. K.; Jones, D. E.; Martin-Castro, A. M. Eur. J. Org. Chem. 2000, 2939.