Synthesis of chiral 2-methyl-5,6,7,8-tetrahydroquinolines from naturally occurring monoterpenes

Arkivoc

Volumn 2004, Issue 14, 2004, Pages 44-50

  Chelucci, Giorgio ^a   Orrù, Gianmauro ^a   Soccolini, Franco ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

Chiral nitrogen heterocycles; Chiral pyridines; Chiral tetrahydroquinolines; Kr hnke annulation

Indexed keywords

BETA PINENE; CAMPHOR; PICOLINE DERIVATIVE; QUINOLINE DERIVATIVE; TERPENE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHIRALITY; EVALUATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 5044227255     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (14)

1. For a recent review on pyridine-phosphine ligands, see: Chelucci, G.; Orrù, G.; Pinna, G. A. Tetrahedron 2003, 59, 9471.
2. Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989.
3. Kröhnke, F. Synthesis 1976, 1and references therein.
4. Kröhnke, F.; Schmidt, E.; Zecher, W. Chem. Ber. 1964, 97, 1163.
5. Saxena, J. P.; Gelra, M. A. Aust. J. Chem. 1967, 20, 1171.
6. Gianini, M.; von Zelewsky, A. Synthesis 1996, 702.
7. (a) Grimshaw, N.; Grimshaw, J. T.; Juneja, H. R. J. Chem. Soc., Perkin Trans. 1 1972, 50.
8. (b) Brown, H. C.; Weissman, S. A.; Perumal, P. T.; Dhokte, U. P. J. Org. Chem 1990, 55, 1217.
9. Chelucci, G.; Gladiali, S.; Marchetti, M. J. Heterocyclic Chem. 1988, 25, 1761.
10. Chelucci, G.; Delogu, G.; Gladiali, S.; Soccolini, F. J. Heterocyclic Chem. 1986, 23, 1395.
11. For the method on related 2-picoline, see: Newkome, G. R. Chem. Rev. 1993, 93, 2067.
12. For references on the synthesis of chiral pyridine derivatives, see: Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
13. Bessière-Chrétien, Y.; Grison, C. Bull. Soc. Chim. Fr. 1970, 3103.
14. Newkome G. R.; Fishel, D. L. J. Org. Chem. 1996, 31, 677.