Lewis acid mediated diastereoselective allylation of 3- menthyloxycarbonyl-5,6-dihydropyridin-4-ones

Synlett

Volumn , Issue 4, 1999, Pages 405-408

  Brocherieux Lanoy, Sylvie ^a   Dhimane, Hamid ^a   Vanucci Bacqué, Corinne ^a   Lhommet, Gérard ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Chiral auxiliaries; Dihydropyridone; Lewis acid; Sakurai allylation; Stereoselective

Indexed keywords

ALLYL COMPOUND; DIHYDROPYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032897645     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2623     Document Type: Article

References (14)

1. David, M.; Dhimane, H.; Vanucci-Bacqué, C.; Lhommet, G. Synlett 1998, 206.
2. Brocherieux-Lanoy, S. PhD Thesis of Université de Paris VI, 4 July 1997.
3. Sato, M.; Aoyagi, S.; Yago, S.; Kibayashi, C. Tetrahedron Lett. 1996, 37, 9063.
4. Treatment of 2a by N,N-dimethylaniline, pyridine or DBU did not affect the starting material.
5. Taber, D. F.; Amedio, J. C.; Gulino, F. J. Org. Chem. 1989, 54, 3474.
6. Seebach, E.; Hungerbühler, E.; Naef, R.; Schnurrenberger, P.; Weidmann, B.; Züger, M. Synthesis 1982, 138.
7. Chavan, S. P.; Zubaidha, P. S.; Dantale, S. W.; Ravindranathan T.; Keshavaraja, A.; Ramaswamy, A. V. Tetrahedron Lett. 1996, 37, 233.
8. The diastereoselectivity of the obtained adducts is not yet ascertained.
9. 5; C 71.53, H 9.80, N 2.78; found C 71.66, H 9.91, N 2.73.
10. (a) Lukes, R.; Smetackova, M. M. Collect. Czech. Chem. Commun. 1934, 6, 231.
11. (b) Comins, D. L.; Hong, H.; Salvador, J. M. J Org. Chem. 1991, 56, 7197.
12. When the reaction mixture of 7a (entry c) was quenched at r.t. with water, debenzyloxycarbonylation took easily place leading to the corresponding free amine. The latter was then converted to the (+)-menthyl carbamate 7b, thus allowing the correlation with compound obtained from substrate 5b.
13. 3). Ooi, T.; Uragushi, D.; Kagoshima, N.; Maruaka, K. J. Am. Chem. Soc. 1998, 120, 5727.
14. Similar conformation for the carbamate moiety has been assumed in the case of 1-(8-phenylmenthyl)oxycarbonyl-3-triiso-propylsilylpyridinium salts derivatives by D. Comins et al: Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.