Dithiane additions to vinyl epoxides: Steric control over the SN2 and SN2′ manifolds

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14516-14517

  Smith III, Amos B ^a   Pitram, Suresh M ^a   Gaunt, Matthew J ^a   Kozmin, Sergey A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

ALCOHOLS; EPOXY COMPOUNDS; LITHIUM; QUINOLIZINES; STEREOISOMERISM; SULFUR COMPOUNDS; VINYL COMPOUNDS;

EID: 0037065361     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0283100     Document Type: Article

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29. Experiments conducted without HMPA were either low-yielding (as was the case for 1a and 1b) or gave no reaction (1c-f). For an insightful discussion of the ion pair solution structures of 2-lithio-1,3-dithianes in THF and HMPA/THF, see: (a) Reich, H. J.; Borst, J. P.; Dykstra, R. R. Tetrahedron 1994, 50, 5869. (b) Sikorski, W. H.; Reich, H. J. J. Am. Chem. Soc. 2001, 123, 6527. (c) Reich, H. J.; Sanders, A. W.; Fiedler, A. T.; Bevan, M. J. J. Am. Chem. Soc. 2002, 124 (45), 13386.
30. Experiments conducted without HMPA were either low-yielding (as was the case for 1a and 1b) or gave no reaction (1c-f). For an insightful discussion of the ion pair solution structures of 2-lithio-1,3-dithianes in THF and HMPA/THF, see: (a) Reich, H. J.; Borst, J. P.; Dykstra, R. R. Tetrahedron 1994, 50, 5869. (b) Sikorski, W. H.; Reich, H. J. J. Am. Chem. Soc. 2001, 123, 6527. (c) Reich, H. J.; Sanders, A. W.; Fiedler, A. T.; Bevan, M. J. J. Am. Chem. Soc. 2002, 124 (45), 13386.
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39. See Supporting Information for the details of the chemical correlation.