Cobalt-mediated [3 + 2]-annulation reaction of alkenes with α,β-unsaturated ketones and imines

Organic Letters

Volumn 11, Issue 16, 2009, Pages 3698-3700

  Schomaker, Jennifer M ^a   Toste, F Dean ^a   Bergman, Robert G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; COBALT; CYCLOALKANE DERIVATIVE; IMINE; KETONE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; COBALT; CYCLOPARAFFINS; IMINES; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 68949086065     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901542n     Document Type: Article

References (16)

1. For selected references, see: (a) Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371-5372.
2. (b) Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2006, 128 (17), 5604-5605.
3. (c) Trost, B. M., Fleming, I., Eds.; Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 1, Part 1.
4. For examples of metal-promoted 1,3-additions to enals see: Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 14030, and references therein. For other selected references on vinyl dianion equivalents,
5. see: (a) Lightfoot, A. P.; Maw, G.; Thirsk, C.; Twiddle, S. J. R.; Whiting, A. Tetrahedron Lett. 2003, 44, 7645.
6. (b) Chambert, S.; Désiré, J.; Décout, J. Synthesis 2002, 16, 2319.
7. Schomaker, J. M.; Boyd, W. C.; Stewart, I. C.; Toste, F. D.; Bergman, R. G. J. Am. Chem. Soc. 2008, 130, 3777.
8. First reported examples of cobalt dinitrosyl and dinitrosoalkane complexes: (a) Brunner, H. J. Organomet. Chem. 1968, 12, 517.
9. (b) Brunner, H.; Loskot, S. Angew. Chem., Int. Ed. Engl. 1971, 10, 515.
10. (c) Brunner, H.; Loskot, S. J. Organomet. Chem. 1973, 61, 401.
11. 2-Cyclopenten-1-one afforded only the conjugate addition product, and 2-cyclohepten-1-one gave a 22% yield of fused-ring product and 48% of the acyclic product (see Supporting Information).
12. Structure confirmed by X-ray structure analysis (see Supporting Information).
13. Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913.
14. (a) Becker, P. N.; Bergman, R. G. Organometallics 1983, 2, 787.
15. (b) Becker, P. N.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 2985.
16. 4 furnished the corresponding diamine in 66% yield (see Supporting Information for details).