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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 3-4
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Original Articles

SN2′ Addition of Organometallic Reagents to β′-Amino Cyclohexenyl Sulfone Derivatives

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Pages 403-416 | Received 20 May 1988, Published online: 23 Oct 2006

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  • Hardinger , S. A. Unpublished results.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

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