Scope and limitation of the [1,4] SPh shift in the synthesis of allylic alcohols

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 1117-1120

  Eames, Jason ^a   De Las Heras, Maria A ^a   Jones, Ray V H ^b   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; ALKANOL;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030019411     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02319-4     Document Type: Article

References (8)

1. Eliel, E. L.; Pearson, W. H.; Jewell, L. M.; Abatjoglou, A. G. Tetrahedron Lett., 1980, 21, 331-334.
2. Djakovitch, L.; Eames, J.; Jones, R. V. H.; McIntyre, S.; Warren, S. Tetrahedron Lett., 1995, 36, 1723-1726.
3. Of course, what is exo to the sulphonium ring in the spirocyclic intermediate 3 is endo to the cyclohexane ring and vice versa.
4. Aggarwal, V. K.; Coldham, I.; McIntyre, S.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1991, 451-460.
5. A typical procedure is given in reference 2.
6. Eliel, E. L.; Hutchins, R. O.; Mebane, R.; Willer, R. L. J. Org. Chem., 1976, 41, 1052-1057.
7. See Hannaby, M.; Judson, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1992, 2609-2614.
8. Brownbridge, P.; Hodgson, P. K. G.; Shepherd, R.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1976, 2024-2034.