Diastereoselective addition of higher order cuprates and zinc-copper reagents to imines derived from (S)-1-phenylethylamine

Tetrahedron

Volumn 55, Issue 26, 1999, Pages 8103-8110

  Bandini, Marco ^a   Cozzi, Pier Giorgio ^a   Umani Ronchi, Achille ^a   Villa, Marzia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Chiral amines; Diastereoselection; Higher order cuprates; Imines; Zinc copper reagents

Indexed keywords

ALPHA METHYLBENZYLAMINE; COPPER DERIVATIVE; COPPER ION; REAGENT; ZINC; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033603413     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00418-4     Document Type: Article

References (25)

1. [1] Bloch R, Chem. Rev. 1998; 98:1407-1438.
2. [2] Enders D, Reinhold U. Tetrahedron:Asymmetry 1997; 8:1895-1946, and references therein .
3. [3] a) Alvaro G, Savoia D, Valentinetti MR. Tetrahedron 1996;52:12571-12586.
4. b) Bocoum A, Boga C, Savoia D, Umani-Ronchi A. Tetrahedron Lett. 1991,32:1367-1370.
5. c) Basile T, Bocoum A, Savoia D, Umani-Ronchi A. J. Org. Chem. 1994;59:7766-7774.
6. d) Alvaro G, Grepioni F, Savoia D. J. Org. Chem. 1997;62:4180-4182.
7. e) Alvaro G, Pacioni, Savoia D. Chem. Eur. J. 1997;3:726-731.
8. f) Alvaro G, Boga C, Savoia D, Umani-Ronchi A. J. Chem. Soc., Perkin Trans. I 1996;875-882.
9. [4] a) Yamamoto Y, Nishii S, Maruyama K, Komatsu T, Ito W. J.Am.Chem.Soc. 1986;108:7778-7786.
10. b) Juaristi E, Escalante J, Leòn-Romo JL, Reyes A. Tetrahedron:Asymmetry 1998; 9:715-740.
11. [5] a) Yamamoto Y. Angew.Chem.,Int.Ed.Engl. 1986; 25:947-959.
12. b) Lipshutz BH. Organometallics in Synthesis. Wiley, Chichester;, 1994:283-382.
13. [6] Knochel P, Singer R. Chem. Rev. 1993; 93: 2117-2188, and references therein.
14. 2 were prepared and tested in the addition with imines, but they afforded the corresponding amines in very low yields.
15. [8] Gao Y, Sato F. J.Org.Chem. 1995, 60: 8136-8137.
16. [9] Alcón M, Canas M, Poch M, Moyano A, Pericàs MA, Riera A. Tetrahedron Lett. 1994;35:1589-1592.
17. [10] Yeh MCP, Chen HG, Knochel P. Organic Syntheses. Wiley, New York; Vol 70, 1992:195-203.
18. 2Me were also prepared but unfortunately they showed low reactivity with imines 1a,c,e and g.
19. [12] a) Stella L, Abraham H. Tetrahedron Lett. 1990; 31:2603-2606.
20. b) Stella L, Abraham H. Tetrahedron 1992;48:9707-9718.
21. [13] Rasmussen KG, Hazell R, and Jørgensen KA. J. Chem. Soc., Chem. Commun. 1997, 1103-110 4.
22. [14] a) Ranu BC, Sarkar A, Majee A. J.Org.Chem. 1997; 62:1841-1842.
23. b) Hattori K, Yamamoto H. Tetrahedron 1993;49:1749-1760.
24. [15] Marshall JA, Shearer BG, Crooks SL. J.Org.Chem. 1987;52:1236-1245 .
25. [16] The preparation of the Zn-Cu reagent 8c and its addition to the imine 1g was carried out as described in the experimental section for the organometallic 8a.