Asymmetric decarboxylative claisen rearrangement reactions of sulfoximine-substituted allylic tosylacetic esters

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6827-6832

  Craig, Donald ^a   Grellepois, Fabienne ^a   White, Andrew J P ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERS; MOLECULAR STRUCTURE; REACTION KINETICS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ACETYL RESIDUES; ALLYLIC ACETATE ESTERS; CLAISEN REARRANGEMENT; SULFOXIMINE MOIETY;

ESTERS;

ESTER DERIVATIVE; SULFOXIDE;

ARTICLE; CLAISEN REARRANGEMENT; DECARBOXYLATION; DRUG ISOLATION; REACTION ANALYSIS; RESIDUE ANALYSIS; SIALYLATION; STEREOCHEMISTRY; STOICHIOMETRY; X RAY CRYSTALLOGRAPHY;

EID: 23644434255     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050747d     Document Type: Article

References (46)

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9. (h) For highly diastereoselective thio-Claisen rearrangement reactions of ketene aminothioacetals, and leading references, see: Nowaczyk, S.; Alayrac, C.; Reboul, V.; Metzner, P.; Averbuch-Pouchot, M.-T. J. Org. Chem. 2001, 66, 7841-7848.
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26. Sulfoximine 4b was prepared by oxidative imination of the corresponding sulfoxide with hydrazoic acid; see: Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418-7423.
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28. Sulfoximine 5b was prepared by oxidation of the corresponding sulfilimine. (a) For the preparation of pyridylsulfilimines, see: Furukawa, N.; Takahashi, F.; Kawai, T.; Kishimoto, K.; Ogawa, S.; Oae, S. Phosphorus Sulfur Relat. Elem. 1983, 16, 167-180.
29. 4 as oxidant, see ref 7c.
30. For details see the Supporting Information.
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34. (d) See ref 6i.
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37. As previously noticed by Bolm and co-workers, moisture should be avoided; see refs 11b,c.
38. Due to their instability, acids 7a-h were isolated by simple extractive workup and were used rapidly without further purification.
39. Use of EDCI in combination of DMAP or HOBt gave the esters in lower yields. For example, esterification of 7a under these conditions gave 8a in 62-64% yield.
40. Esters 8a-h were stored in a freezer due to their instability toward decarboxylation, regenerating the starting sulfoximines 3b-g, 4b, or 6.
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43. For ambient-temperature decarboxylative Claisen rearrangement reactions of sulfone derivatives containing an additional electron-withdrawing group on the α-position, see: Craig, D.; Grellepois, F. Org. Lett. 2005, 7, 463-465.
44. Trost, B. M.; Matsuoka, R. T. Synlett 1992, 27-30.
45. S,3R)-9m only the relative stereochemistry could be determined with certainty.
46. S,2S) configuration in the aryl-substituted products because of the change in priority of substituents on the stereocenter.