Sulfoxide-controlled S N2′ displacements between cuprates and vinyl and alkynyl epoxy sulfoxides

Tetrahedron

Volumn 60, Issue 37, 2004, Pages 8171-8180

  Fernández De La Pradilla, Roberto ^a   Viso, Alma ^a   Castro, Sonia ^a   Fernández, Jorge ^a   Manzano, Pilar ^a   Tortosa, Mariola ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Allenes; Asymmetric S N2 ; Cuprate; Epoxide; Sulfoxide

Indexed keywords

ALKYNYL GROUP; COPPER DERIVATIVE; EPOXIDE; SULFOXIDE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 4143071578     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.092     Document Type: Article

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39. The stereochemical assignment of diastereomers 6a and 6b is tentative since extensive decomposition upon storage at room temperature along with the low stereoselectivity found, could indicate a favourable [2,3]-sigmatropic rearrangement of the propargylic sulfoxides with loss of the stereochemical integrity at sulfur.
40. N2′ reactivity of these substrates.
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42. These results seems to indicate a higly stereocontrolled pathway of the allylic displacement. The structural assignment of 14a,b was made on the basis of an anti attack, however, we cannot accurately establish the stereochemical outcome since the structural assignment for 6a,b is tentative, see Ref. 11.
43. Structural assignments of the products are based in the comparison of NMR data with that of related hydroxy vinyl sulfoxides from our group previously characterized by X-ray diffraction analysis. The Z-E stereochemistry is easily established through the chemical shifts of vinyl protons. For example 7a (H-3): 6.17 ppm; 11a (H-3): 6.43 ppm. Significant differences are also found for H-2 protons in these compounds.
44. Additional data (i.e., X-ray) will be needed for unequivocal structural assignment of this compound.
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