Sulfinyl-mediated chirality transfer in diastereoselective claisen rearrangements

Organic Letters

Volumn 4, Issue 14, 2002, Pages 2373-2376

  Fernández De La Pradilla, Roberto ^a   Montero, Carlos ^a   Tortosa, Mariola ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

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ARTICLE;

EID: 3242740711     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0261130     Document Type: Article

References (47)

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23. For convenience, most experiments were conducted with racemic sulfoxides. Enantiopure (E)-sulfinyl alcohols were prepared (70-80%) from vinyl sulfoxides (Craig, D.; Daniels, K.; McKenzie, A. R. Tetrahedron 1993, 49, 11263-11304) by treatment with LDA and an aldehyde. Racemic (Z)-sulfinyl alcohols were prepared (52-60%) from the corresponding alkynyl sulfides (Kabanyane, S. T.; MaGee, D. I. Can. J. Chem. 1992, 70, 2758-2763) by Pd-catalyzed hydroestannylation (Magriotis, P. A.; Brown, J. T.; Scott, M. E. Tetrahedron Lett. 1991, 32, 5047-5051), tin-lithium exchange, condensation with an aldehyde, and diastereoselective oxidation with mCPBA. For an enantioselective synthesis of (Z)-sulfenyl alcohols, see: Berenguer, R.; Cavero, M.; Garcia, J.; Muñoz, M. Tetrahedron Lett. 1998, 39, 2183-2186.
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25. For convenience, most experiments were conducted with racemic sulfoxides. Enantiopure (E)-sulfinyl alcohols were prepared (70-80%) from vinyl sulfoxides (Craig, D.; Daniels, K.; McKenzie, A. R. Tetrahedron 1993, 49, 11263-11304) by treatment with LDA and an aldehyde. Racemic (Z)-sulfinyl alcohols were prepared (52-60%) from the corresponding alkynyl sulfides (Kabanyane, S. T.; MaGee, D. I. Can. J. Chem. 1992, 70, 2758-2763) by Pd-catalyzed hydroestannylation (Magriotis, P. A.; Brown, J. T.; Scott, M. E. Tetrahedron Lett. 1991, 32, 5047-5051), tin-lithium exchange, condensation with an aldehyde, and diastereoselective oxidation with mCPBA. For an enantioselective synthesis of (Z)-sulfenyl alcohols, see: Berenguer, R.; Cavero, M.; Garcia, J.; Muñoz, M. Tetrahedron Lett. 1998, 39, 2183-2186.
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43. This methodology entails 3-4 steps, for 5-E isomers, or 6-7 steps, for 5-Z isomers, from commercially available starting materials. For selected synthetic applications of alkenyl sulfoxides, see: (a) Asymmetric Pauson-Khand: Carretero, J. C.; Adrio, J. Synthesis 2001, 1888-1896.
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