Synthesis of enantiomerically pure β-hydroxy-γ-sulfinylaldehyde dimethyl acetals

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1819-1828

  García Ruano, José L ^a   Maestro, M Carmen ^a   Barros, David ^a   González Vadillo, Ana M ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; BETA OXOSULFOXIDE DERIVATIVE; LITHIUM; PROPIONIC ACID DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 0342468282     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00217-0     Document Type: Article

References (37)

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8. th European Symposium on Organic Chemistry. Barcelona. Spain.
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19. The formation of compounds with a similar structure to that of 6 must be responsible of the low yields obtained by Page in similar reactions reported in reference 6
20. 1H-NMR data and those of the E and Z isomers of 3-p-tolylsulfinyl-2-butenal dimethyl acetal (see ref. 4).
21. We have checked that in the presence of LDA, compound 1 readily evolves into compound 9.
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23. 2 3.85 (5a) 3.92 (5b) 1.32(5a) 1.20 (5b) This report
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25. S enantiomer at 3.37 ppm.
26. Usually, the preparation of optically active allyl aryl sulfoxides is complicated by its configurational instability. See: a) Bickart, P. Carson, F.V.; Jacobus, J.; Miller, E.G.; Mislow, K.; J. Amer. Chem. Soc., 1968, 90, 4869.
27. b): Mislow, K.; Tang, R.; J. Amer. Chem. Soc., 1970, 92, 2100. In addition, the obtained allylsulfoxides are stable compounds presumably because sulfoxide-sulfenate rearrangement is unfavourable by the withdrawing effect of the methoxycarbonyl group.
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31. 3S: 316.11332. Found: 316.11282.
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35. 2 reductions of γ-methoxycarbonyl and γ-alkoxy β-ketosulfoxides (Solladié, G.; Almario, A., Tetrahedron Letts., 1992, 33, 2477; Solladié, G.; Almario, A., Tetrahedron Asymmetry, 1994, 5, 1717).
36. 2 reductions of γ-methoxycarbonyl and γ-alkoxy β-ketosulfoxides (Solladié, G.; Almario, A., Tetrahedron Letts., 1992, 33, 2477; Solladié, G.; Almario, A., Tetrahedron Asymmetry, 1994, 5, 1717).
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