Preparation of chiral-at-iron-substituted allyl and vinyl sulfones. Subsequent enolate generation and stereo-and regioselective alkylation

Organometallics

Volumn 16, Issue 21, 1997, Pages 4519-4521

  Patel, Paren P ^a   Welker, Mark E ^a   Liable Sands, Louise M ^b   Rheingold, Arnold L ^b  

^a WAKE FOREST UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000961964     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970448h     Document Type: Article

References (23)

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3. (c) For an earlier report on iron dienyl complexes prepared by a different route, see: Waterman, P. S.; Belmonte, J. E.; Bauch, T. E.; Belmonte, P. A.; Giering, W. P. J. Organomet. Chem. 1985, 294, 235.
4. Piper, T. S.; Wilkinson, G. J. Inorg. Nucl. Chem. 1956, 3, 104.
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6. Simpkins, N. S. Sulfones in Organic Synthesis; Pergamon: Oxford, 1993; Chapter 2.
7. (a) Herriott, A. W.; Picker, D. Synthesis 1975, 447.
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10. 4S: C, 53.65; H, 3.94. Found: C, 53.56; H, 4.00.
11. w = 0.1313, GOF = 1.327.
12. +): 593.1003. Found: 593.1016.
13. w = 0.0805, GOF = 0.864. Some sulfoxide-containing chiral-at-iron acyls have been reported previously, but to our knowledge these chiral at iron alkenyl sulfones are unknown, see: (a) Davies, S. G.; Gravatt, G. L. J. Chem. Soc., Chem. Commun. 1988, 780.
14. (b) Baker, R. W.; Davies, S. G. Tetrahedron: Asymmetry 1993, 4, 1479.
15. Chiral-at-iron sulfonyl complexes (analogous to the acyls) have also been reported, see: Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
16. 3) auxiliary, see: Blackburn, B. K.; Davies, S. G.; Whittaker, M. In Stereochemistry of Organometallic Inorganic Compounds 3; Bernal, I., Ed.; Elsevier, Amsterdam, 1989; pp 141-223.
17. +): 607.1135. Found: 607.1128.
18. (a) Reference 4, pp 111-118.
19. (b) Savoia, D.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Perkin Trans. 1 1977, 123.
20. (c) Jonczyk, A.; Radwan-Pytlewski, T. J. Org. Chem. 1983, 48, 910.
21. (d) Hayakawa, K.; Nishiyama, H.; Kanematsu, K. J. Org. Chem. 1985, 50, 512.
22. (e) Trost, B. M.; Schmuff, N. R. J. Am. Chem. Soc. 1985, 107, 396.
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