Sequential stereoselective catalysis: Two single-flask reactions of a substrate in the presence of a bifunctional chiral ligand and different transition metals

European Journal of Organic Chemistry

Volumn , Issue 8, 2003, Pages 1428-1432

  Annunziata, Rita ^a   Benaglia, Maurizio ^a   Cinquini, Mauro ^a   Cozzi, Franco ^a   Puglisi, Alessandra ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Bifunctional ligand; Chiral ligands; Cyclopropanation; Dihydroxylation; Stereoselective catalysis

Indexed keywords

3 (4 VINYLPHENYL)PROPENOATE; ALKENE; DIHYDROQUINIDINE; LIGAND; OXAZOLINE DERIVATIVE; PROPYLENE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLOPROPANATION; DIHYDROXYLATION; ELECTRON; STEREOCHEMISTRY;

EID: 0038301158     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390201     Document Type: Article

References (22)

1. Review: Comprehensive Asymmetric Catalysis, vol. I-IV (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
2. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, Eur. J. Org. Chem. 2001, 1045-1048.
3. The possibility of performing sequential stereoselective catalytic processes was reported for the first time using a copolymeric catalyst by: [3al H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501. For more recent results obtained with supported ligands see: [3b] B. M. Choudary, N. S. Chowdary, S. Madhi, M. N. Kantam, Angew. Chem. Int. Ed. 2001, 40, 4620-4623. [3c] B. M. Choudary, N. S. Chowdary, K. Jyothi, N. S. Kumar, M. N. Kantam, Chem. Commun. 2002, 586-587; and references therein.
4. The possibility of performing sequential stereoselective catalytic processes was reported for the first time using a copolymeric catalyst by: [3al H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501. For more recent results obtained with supported ligands see: [3b] B. M. Choudary, N. S. Chowdary, S. Madhi, M. N. Kantam, Angew. Chem. Int. Ed. 2001, 40, 4620-4623. [3c] B. M. Choudary, N. S. Chowdary, K. Jyothi, N. S. Kumar, M. N. Kantam, Chem. Commun. 2002, 586-587; and references therein.
5. The possibility of performing sequential stereoselective catalytic processes was reported for the first time using a copolymeric catalyst by: [3al H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000, 122, 6500-6501. For more recent results obtained with supported ligands see: [3b] B. M. Choudary, N. S. Chowdary, S. Madhi, M. N. Kantam, Angew. Chem. Int. Ed. 2001, 40, 4620-4623. [3c] B. M. Choudary, N. S. Chowdary, K. Jyothi, N. S. Kumar, M. N. Kantam, Chem. Commun. 2002, 586-587; and references therein.
6. For reviews describing related approaches see: [4a] M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989-1999 ("asymmetric two-center catalysis"). [4b] G. J. Rowlands, Tetrahedron 2001, 57, 1865-1882 ("ambifunctional cooperative catalysis").
7. For reviews describing related approaches see: [4a] M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989-1999 ("asymmetric two-center catalysis"). [4b] G. J. Rowlands, Tetrahedron 2001, 57, 1865-1882 ("ambifunctional cooperative catalysis").
8. M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901.
9. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, M. Pitillo, J. Org. Chem. 2001, 66, 3160-3166.
10. D. A. Evans, K. A. Worpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728.
11. The assignment was tentatively based on the assumption that the enantiofacial preference of the Evans' cyclopropanation reaction was the same for 10 and styrene; it must be noted that (R,R)-11 and the major trans adduct obtained from styrene both had strong negative optical rotations.
12. H. Kwong, C. Sorato, Y. Ogino, H. Chen, K. B. Sharpless, Tetrahedron Lett. 1990, 31, 2999-3002.
13. We are well aware of the fact that other ligands (e.g. PHALDHQD) secure higher stereoselectivity in this reaction. Nevertheless, we considered dihydroquinidine 4-chlorobenzoate a good structural analog of ligand 9.
14. For previous examples of asymmetric dihydroxylation reactions proceeding with kinetic resolution see: [11a] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, F. Ponzini, Biorg. Med. Chem. Lett. 1993, 11, 2397-2402. [11b] M. S. Van-Nieuwenhze, K. B. Sharpless, J. Am. Chem. Soc. 1993, 115, 7864-7865. [11c] E. J. Corey, M. C. Noe, A. Guzman-Perez, J. Am. Chem. Soc. 1995, 117, 10817-10824.
15. For previous examples of asymmetric dihydroxylation reactions proceeding with kinetic resolution see: [11a] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, F. Ponzini, Biorg. Med. Chem. Lett. 1993, 11, 2397-2402. [11b] M. S. Van-Nieuwenhze, K. B. Sharpless, J. Am. Chem. Soc. 1993, 115, 7864-7865. [11c] E. J. Corey, M. C. Noe, A. Guzman-Perez, J. Am. Chem. Soc. 1995, 117, 10817-10824.
16. For previous examples of asymmetric dihydroxylation reactions proceeding with kinetic resolution see: [11a] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, F. Ponzini, Biorg. Med. Chem. Lett. 1993, 11, 2397-2402. [11b] M. S. Van-Nieuwenhze, K. B. Sharpless, J. Am. Chem. Soc. 1993, 115, 7864-7865. [11c] E. J. Corey, M. C. Noe, A. Guzman-Perez, J. Am. Chem. Soc. 1995, 117, 10817-10824.
17. For a general treatment of double stereoselection and the definition of matched and mismatched pairs see: S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.
18. On the basis of these stereochemical results it could be anticipated that a ligand such as 9 prepared starting from either bis(oxazoline) 4 and dihydroquinine or (less practically) from ent-4 and dihydroquinidine would provide a more stereoselective overall process in which the stereochemical preference of the osmylation reaction matches that of the cyclopropane substrate 11.
19. VI salt has previously been considered and found to be negligible (see ref. [2]).
20. This yield is only slightly lower than that calculated for the mixture of the trans-cyclopropanediols obtained performing the reactions separately (27.8%). In a control experiment the reactions were repeated sequentially in one flask, operating as described in the case of 9, and using bis(oxazoline) 6 and dihydroquinidine 4-chlorobenzoate as the ligands. From this experiment the trans-cyclopropanediols were isolated in 21% yield as an 80:20 mixture of diastereoisomers.
21. As suggested by one referee, in the cyclopropanation reaction the active catalyst may bind to a molecule of substrate via the osmate, and it would be cleaved on addition of water in the second step.
22. DE Patent 2340601, 1973, Chem. Abstr. 1973, 80, 145713.