Highly enantioselective catalytic dynamic resolution of N-boc-2-lithiopiperidine: Synthesis of (R)-(+)- N-boc-pipecolic acid, (S)-(-)-coniine, (S)-(+)-pelletierine, (+)-β-conhydrine, and (S)-(-)-ropivacaine and formal synthesis of (-)-lasubine II and (+)-cermizine C

Journal of the American Chemical Society

Volumn 132, Issue 35, 2010, Pages 12216-12217

  Beng, Timothy K ^a   Gawley, Robert E ^a  

^a UNIVERSITY OF ARKANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL LIGAND; DIASTEREOMERS; DYNAMIC RESOLUTION; ELECTROPHILES; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; FORMAL SYNTHESIS; PIPECOLIC ACID; ROPIVACAINE;

ACIDS;

ALKALOID DERIVATIVE; CERMIZINE C; CONHYDRINE; CONIINE; ELECTROPHILE; LASUBINE II; PELLETIERINE; PIPECOLIC ACID DERIVATIVE; ROPIVACAINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYTIC DYNAMIC RESOLUTION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; STOICHIOMETRY;

ALKALOIDS; AMIDES; CATALYSIS; HETEROCYCLIC COMPOUNDS, 2-RING; LITHIUM; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PIPECOLIC ACIDS; PIPERIDINES; QUINOLIZINES; STEREOISOMERISM; THERMODYNAMICS;

EID: 77956245191     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja105772z     Document Type: Article

References (15)

1. Beak, P. and Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197
2. Kerrick, S. T. and Beak, P. J. Am. Chem. Soc. 1991, 113, 9708
3. Bailey, W. F., Beak, P., Kerrick, S. T., Ma, S., and Wiberg, K. B. J. Am. Chem. Soc. 2002, 124, 1889
4. Stead, D., Carbone, G., OBrien, P., Campos, K. R., Coldham, I., and Sanderson, A. J. Am. Chem. Soc. 2010, 132, 7260
5. Coldham, I., Raimbault, S., Chovatia, P. T., Patel, J. J., Leonori, D., Sheikh, N. S., and Whittaker, D. T. E. Chem. Commun. 2008, 4174
6. Lee, W. K., Park, Y. S., and Beak, P. Acc. Chem. Res. 2009, 42, 224.
7. Coldham, I. and Sheikh, N. S. In Topics in Stereochemistry; Gawley, R. E., Ed.; VHCA: Zurich, 2010; Vol. 26, p 253.
8. Beng, T. K., Yousaf, T. I., Coldham, I., and Gawley, R. E. J. Am. Chem. Soc. 2009, 131, 6908
9. A mechanistic study of the DTR and CDR of rac-2 will be published elsewhere.
10. Gawley, R. E. Tetrahedron Lett. 1999, 40, 4297
11. Rein, K. S., Chen, Z.-H., Perumal, P. T., Echegoyen, L., and Gawley, R. E. Tetrahedron Lett. 1991, 32, 1941
12. Gawley, R. E., Low, E., Zhang, Q., and Harris, R. J. Am. Chem. Soc. 2000, 122, 3344
13. Gawley, R. E., Eddings, D. B., and Santiago, M. Org. Biomol. Chem. 2006, 4, 4285
14. Beak, P. and Lee, W. K. J. Org. Chem. 1993, 58, 1109
15. Cheng, G., Wang, X., Su, D., Liu, H., Liu, F., and Hu, Y. J. Org. Chem. 2010, 75, 1911