Chiral biferrocene-based(oxazolines): Ligands for Cu(I)-catalyzed asymmetric cyclopropanations of ene-diazoacetates

Tetrahedron

Volumn 55, Issue 33, 1999, Pages 10079-10086

  Kim, Sung Gon ^a   Cho, Chang Woo ^a   Ahn, Kyo Han ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2,2'' BIS(4 TERT BUTYL 2 OXAZOLIN 2 YL) 1,1'' BIFERROCENE; 2,2'' BIS(4 TERT BUTYL 2 OXAZOLIN 2 YL) 3,3'' BIS(DIPHENYLHYDROXYMETHYL) 1,1'' BIFERROCENE; AZO COMPOUND; COPPER; COPPER COMPLEX; FERROCENE DERIVATIVE; MALONIC ACID; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CONFORMATION; CONTACT ANGLE; ENANTIOMER; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033551816     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00542-6     Document Type: Article

References (22)

1. Kim SG, Cho CW, Ahn KH. Tetrahedron: Asymmetry 1997;8:1023.
2. Gant TG, Noe MC, Corey EJ. Tetrahedron Lett. 1995;36:8745.
3. Uozumi Y, Kyota H, Kishi E, Kitayama K, Hayashi T. Tetrahedron: Asymmetry 1996;7:1603.
4. (a) Doyle MP. Recl. Trav. Chim. Pay-Bas 1991;110:305.
5. (b) Doyle MP. Aldrichimica Acta 1996;29:3.
6. (c) Doyle MP, Peterson CS, Parker Jr DL. Angew. Chem. Int. Ed. Engl. 1996;35:1334.
7. (a) Richards C, Damalidis T; Hibbs, DE., Hursthose MB. Synlett 1995;74.
8. (b) Sammakia T, Latham HA, Schaad DR. J. Org. Chem. 1995;60:10.
9. (c) Nishibayashi Y, Uemura S. Synlett 1995;79,
10. (d) Park J, Lee S, Ahn KH, Cho CW. Tetrahedron Lett. 1995;36:7263,
11. (e) Ahn KH, Cho CW, Baek HH, Park J, Lee S. J. Org. Chem. 1996;61:4937.
12. Coleman RS, Grant EB. Tetrahedron Lett. 1993;34:2225.
13. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. Recently monoferrocenyl analogs were successfully used as chiral ligands in enantioselective diethylzinc addition reactions, see: Bolm C, Muñiz-Fernández K, Seger A, Raabe G, Günther K. J. Org. Chem. 1998;63:7860.
14. Evans DA, Woerpel KA, Scott MJ. Angew. Chem. Int. Ed. Engl. 1992;31:430.
15. Woerpel KA. In Ph. D. thesis. Harvard University;1992;54.
16. MacSpartan plus® from Wavefunction, Inc. (http://www.wavefun.com) was used as the modeling program.
17. Fritschi H, Leutenegger U, Pfaltz A. Helv. Chim. Acta 1988;71:1553.
18. Evans DA, Woerpel KA, Hinman, MM, Faul MM. J. Am. Chem, Soc. 1991;113:726.
19. Mori K, Matsui M. Tetrahedron 1969;25:5013.
20. Pfaltz and co-workers reported 85% ee for the same reaction using a semicorrin-based N,N-chelate: Piqué C, Fähndrich B, Pfaltz A. Synlett 1995;491.
21. 1,1-Disubstituted olefins seemed to be better substrates than mono- and 1,2-disubstituted ones in our case: In the intermolecular case, the cyclopropanation of 1,1-diphenylethene with ethyl diazoacetate gave 78% ee while that of (E)-1-phenylpropene gave 44% ee (major trans-isomer) with ligand 1c: Unpublished results.
22. Lightner DA, Jackman DE. Tetrahedron Lett. 1975;3051.