References
- Fuchs , P. L. and Braish , T. F. 1986 . Chem. Rev. , 86 : 903 Syntheses Via Vinyl Sulfones 35. For a review on this subject see
- Hutchinson , D. K. and Fuchs , P. L. 1985 . J. Amer. Chem. Soc. , 107 : 6137
- Pan , Y. , Hutchinson , D. K. , Nantz , M. H. and Fuchs , P. L. 1988 . Tetrahedron , 44 : 0000 For leading references to these applications see:
- Knapp , S. , Sebastian , M. J. and Ramanathan , H. 1983 . J. Org. Chem. , 48 : 4786
- Hardinger , S. A. Unpublished results.
- Crossland , R. K. and Servis , K. L. 1970 . J. Org. Chem. , 35 : 3195
- For 15a Jbc, Jcd, and Jde are all 10–11Hz, with Jab ca. 1–2Hz.
- Hutchinson , D. K. , Hardinger , S. A. and Fuchs , P. L. 1986 . Tetrahedron Lett. , 27 : 1425 Reaction of 12 with methyl copper (5eq; 8eq) and lithium bromide (2eq) in ether/toluene for 8 h at 0[ddot]C also affords 15a (42%; 82%). Use of lithium dimethyl cuprate (4eq) under similar conditions provides 15a in 35% yield. For amine-directed cuprate additions to cyclopentenyl sulfones see:
- This results in a boat conformation for 16a (characterized as the fluoroborate derivative): Jab=2.2Hz; Jbc=3.0Hz; Jcd=9.4Hz; Jag=7.6Hz.
- Saddler , J. C. and Fuchs , P. L. 1981 . J. Amer. Chem. Soc. , 103 : 2112 The stereochemistry of 17a 18a was also confirmed by comparison to the known ()desilylated alcohols which had been previously assigned on the basis of a europium shift study (Saddler, J. C., Ph. D. Thesis, Purdue University 1982).
- Hutchinson , D. K. and Fuchs , P. L. 1987 . J. Amer. Chem. Soc. , 109 : 4930
- Patt , S. L. and Shoolery , J. N. 1982 . J. Magn. Reson. , 46 : 535