Chiral vinyl dioxazaborocines in synthesis: Asymmetric cuprate additions to β-boronyl acrylates and vinyl sulfones

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4235-4238

  Farthing, Christopher N ^a   Marsden, Stephen P ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Alcohols; Asymmetric synthesis; Boron and compounds; Grignard reagents; Michael reactions

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALCOHOL; ALKENE; BORON DERIVATIVE; COPPER DERIVATIVE; ORGANOMETALLIC COMPOUND; REAGENT; SULFONE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; OXIDATION; SYNTHESIS;

EID: 0034729514     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00572-4     Document Type: Article

References (25)

1. Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1990; Vol. 4, pp.199-236.
2. Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806.
3. Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283-285.
4. See, for example: Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047-4056 and references cited therein.
5. (a) Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986-4989;
6. (b) Pietruszka, J.; Widenmeyer, M. Synlett. 1997, 977-979;
7. (c) Luithle, J. E. A.; Pietruszka, J.; Witt, A. Chem. Commun. 1998, 2651-2652;
8. (d) Zhou, S.-M.; Deng, M.-Z.; Xia, L.-J.; Tang, M.-H. Angew. Chem., Int. Ed. 1998, 37, 2845-2847.
9. (a) Wang, X. J. Chem. Soc., Chem. Commun. 1991, 1515-1516;
10. (b) Bonk, J. D.; Avery, M. A. Tetrahedron: Asymmetry 1997, 8, 1149-1152;
11. (c) Renard, P.-Y.; Lallemand, J.-Y. Tetrahedron: Asymmetry 1996, 7, 2523-2524;
12. (d) Mortier, J.; Vaultier, M.; Plunian, B.; Toupet, L. Heterocycles 1999, 50, 703-711;
13. (e) Guennouni, N.; Rasset, C.; Carboni, B.; Vaultier, M. Synlett 1992, 581-584.
14. (a) Davies, C. D.; Marsden, S. P.; Stokes, E. S. E. Tetrahedron Lett. 1998, 39, 8513-8516;
15. (b) Jiang, B.; Zhang, A.; Kan, Y., Chinese Journal of Chemistry 1999, 17, 293-299;
16. (c) Wallace, R. H.; Zong, K. K. J. Organomet. Chem. 1999, 581, 87-91;
17. (d) Zhang, A.; Kan, Y.; Zhao, G. L.; Jiang, B. Tetrahedron 2000, 56, 965-970;
18. (e) Davies, C. D.; Marsden, S. P.; Stokes, E. S. E. Tetrahedron Lett. 2000, 41, 4229-4233.
19. Guennouni, N.; Lhermitte, F.; Cochard, S.; Carboni, B. Tetrahedron 1995, 51, 6999-7018.
20. Negishi, E.-I.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 6837-6838.
21. Onak, T. Organoborane Chemistry; Academic Press: New York, 1975.
22. The use of β-silyl acrylamides bearing a chiral sultam as a formylacetate equivalent has been reported: Oppolzer, W.; Mills, R. J.; Pachinger, W. Stevenson, T. Helv. Chim. Acta. 1986, 69, 1542-1545.
23. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343.
24. Prepared from benzyl propiolate and p-toluenesulfonylacetylene by the general hydroboration procedure of: Martinez-Fresneda, P.; Vaultier, M. Tetrahedron Lett. 1989, 30, 2929-2932, followed by esterification with pinacol and purification by chromatography/crystallisation, respectively.
25. Koichi, Y.; Suginata, K.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1995, 1645-1646.