Unexpected diastereoselectivity in the formation of 3,5-disubstituted indolizidines by intramolecular reductive amination

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1585-1588

  Celimene C ^a   Dhimane, H ^a   Saboureau, A ^a   Lhommet, G ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE ALKALOID; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

AMINATION; ARTICLE; FROG; HYDROGEN BOND; HYDROGENATION; PRIORITY JOURNAL; QUANTITATIVE DIAGNOSIS; STEREOCHEMISTRY;

EID: 0347621246     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00187-5     Document Type: Article

References (13)

1. Tokuyama, T. ; Nishimori, N. ; Karle, I. L. ; Edwards, M. W. ; Daly J. W. Tetrahedron 1986, 42, 3453.
2. Michael, J. P. Natural Products Reports 1990, 485.
3. Fleurant, A. ; Célérier, J. P. ; Lhommet, G. Tetrahedron : Asymmetry 1993, 4, 1429.
4. Machinaga, N. ; Kibayashi, C. J. Org. Chem. 1992, 57, 5178. Momose, T. ; Toyooka, N. ; Seki, S. ; Hirai, Y. Chem. Pharm. Bull. 1990, 38, 2072.
5. Machinaga, N. ; Kibayashi, C. J. Org. Chem. 1992, 57, 5178. Momose, T. ; Toyooka, N. ; Seki, S. ; Hirai, Y. Chem. Pharm. Bull. 1990, 38, 2072.
6. Célimène, C. ; Dhimane, H. ; LeBail, M. ; Lhommet, G. Tetrahedron Lett. 1994, 35, 6105.Trans and cis isomers of 1 were not separable by chromatography.
7. 2 system in THF/EtOH (1/1). At this stage the pure trans alcohol 2 was isolated in 67% yield. Acetate 3 was prepared from 2 using acetyl chloride in pyridine (92% yield).
8. 2O/Pentane, 3/1).
9. The key intermediate 1 could not be separated from its cis isomer (4%) and therefore 5 was used as a trans/cis (96/4) mixture.
10. 2O/Pentane, 3/1)
11. The two others stereomers were present in too low concentration to be isolated.
12. 4 in THF.
13. 2O gave a complex mixture.