Carbolithiation of an α-amino lithio alkoxide derived from cinnamaldehyde

Synlett

Volumn , Issue 4, 2000, Pages 532-534

  Brémand, Nathalie ^a   Normant, Jean F ^a   Mangeney, Pierre ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Aldehyde; Amination; Carbolithiation; Diastereoselection; Nucleophilic addition

Indexed keywords

ALDEHYDE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS;

EID: 0342264630     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. Norsikian, S.; Marek, I.; Klein, S.; Poisson, J.F.; Normant, J.F. Chem. Eur. J. 1999, 5, 2055-2067.
2. a) Brémand, N.; Marek, I.; Normant, J.F. Tetrahedron Lett. 1999, 40, 3379-3382.
3. b) Brémand, N.; Marek, I.; Normant, J.F. Tetrahedron Lett. 1999, 40, 3383-3386.
4. a) Michael, U.; Gronowitz, S. Acta Chem. Scand. 1968, 1353-1354.
5. b) Barsky, L.; Gschwend, H.W.; Mc Kenna, J.; Rodriguez, H.R. J. Org. Chem. 1976, 41, 3651-3652.
6. c) For a recent use of morpholine amides see : Sengupta, S.; Mondal, S.; Das, D. Tetrahedron Lett. 1999, 40, 4107-4110.
7. Comins, D.L. Synlett 1992, 615-625.
8. Armstrong, D.R.; Davies, J.E.; Davies, R.P.; Raithby, P. R.; Snaith, R.; Wheatley, A. E. H. New J. Chem. 1999, 35-41.
9. For carbolithiations of various styrenes, see ref (1) and a) Knochel, P. In Comprehensive Organic Synthesis, Trost, B. M. Ed.; Pergamon Press,Oxford,1991, p. 865.
10. b) Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021-9024.
11. c) Wei, X.; Taylor, R.J.K. Tetrahedron Lett. 1996, 37, 4209-4210.
12. d) Superchi, S.; Satomayor, N.; Miao, G.; Joseph, B.; Campbell, M. G.; Snieckus, V. Tetrahedron Lett. 1996, 37, 6061-6064.
13. For self-condensation of aldehydes in presence of an amine see: Ishikawa, T.; Uedo, E.; Okada, S.; Saito, S. Synlett 1999, 450-452.
14. Majewski, M.; Gleave, D.M. J. Organomet. Chem. 1994, 470, 1-16.
15. Takeda, K.; Ohnishi, Y.; Koizumi, T. Org. Lett. 1999, 1, 237-240 and references cited herein.
16. Kraus, G.A.; Taschner, M.J. J. Org. Chem. 1980, 45, 1175-1176.
17. Tietze, L.F.; Schneider, C. J. Org. Chem. 1991, 56, 2476-2481.
18. Alexakis, A.; Frutos, J.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326-3330.
19. 3) diastereoisomer I (95%) δ 136.59, 137.68, diastereoisomer 2 (5%) δ 138.32, 138.49.