Stereocontrol in N-directed hydroboration: Synthesis of amino alcohols related to the piperidine alkaloids

Organic Letters

Volumn 11, Issue 5, 2009, Pages 1059-1061

  Wang, Guoqiang ^a   Vedejs, Edwin ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKENE; AMINOALCOHOL; BORANE DERIVATIVE; FUSED HETEROCYCLIC RINGS; PIPERIDINE DERIVATIVE;

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

ALKALOIDS; ALKENES; AMINO ALCOHOLS; BORANES; CATALYSIS; HETEROCYCLIC COMPOUNDS, BRIDGED-RING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM;

EID: 64349124481     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802781c     Document Type: Article

References (12)

1. Scheideman, M.; Shapland, P.; Vedejs, E. J. Am. Chem. Soc. 2003, 125, 10502.
2. Scheideman, M.; Wang, G.; Vedejs, E. J. Am. Chem. Soc. 2008, 130, 8669.
3. Stereoselective amine HB: (a) Lyle, R. E.; Carle, K. R.; Ellefson, C. R.; Spicer, C. K. J. Org. Chem. 1970, 35, 802. Stern, P.; Trska, P.; Ferles, M. Collect. Czech. Chem. Commun. 1974, 39, 2267. Stereoselective N-EWG HB:
4. (b) Fujita, Y.; Irreverre, F.; Witkop, B. J. Am. Chem. Soc. 1964, 86, 1844. Dicko, A.; Montury, M.; Baboulene, M. Tetrahedron Lett. 1987, 28, 6041. Burgess, K.; Ohlmeyer, M. J. J. Org. Chem. 1991, 56, 1027. Evans, D. A.; Fu, G. C. J. Am. Chem. Soc. 1991, 113, 4042. Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115. Hodgson, D. M.; Thompson, A. J.; Wadman, S.; Keats, C. J. Tetrahedron 1999, 55, 10815.
5. Reviews: Bates, R. W.; Sa-Ei, K. Tetrahedron 2002, 58, 5957. Felpin, F.-X.; Lebreton, J. Tetrahedron 2004, 60, 10127.
6. Takahata, H.; Kubota, M.; Ikota, N. J. Org. Chem. 1999, 64, 8594.
7. Maio, W. A.; Sinishtaj, S.; Posner, G. H. Org. Lett. 2007, 9, 2673.
8. Extensive synthetic work targetting piperidine alkaloids is described in ref 4. For selected recent studies, see: (a) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925.
9. (b) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2003, 125, 11276.
10. (c) Lesma, G.; Crippa, S.; Danieli, B.; Passarella, D.; Sacchetti, A.; Silvani, A.; Virdis, A. Tetrahedron 2004, 60, 6437.
11. (d) Passarella, D.; Barilli, A.; Belinghieri, F.; Fassi, P.; Riva, S.; Sacchetti, A.; Silvani, A.; Danieli, B. Tetrahedron: Asymmetry 2005, 16, 2225.
12. Allinger, N. L.; Carpenter, J. G. D.; Karkowski, F. M. J. AM. Chem. Soc. 1965, 87, 1232. Bishop, R. J.; Sutton, L. E.; Dineen, D.; Jones, R. A. Y.; Katritzky, A. R.; Wyatt, R. J. J. Chem. Soc. B 1967, 493.