Highly enantioselective allylation of arylaldehydes catalyzed by a silver(I)-chiral binaphthylthiophosphoramide

European Journal of Organic Chemistry

Volumn , Issue 15, 2003, Pages 2823-2828

  Wang, Chun Jiang ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aldehydes; Allylation; Asymmetric catalysis; N,S ligands; Silver

Indexed keywords

ALCOHOL; ALDEHYDE; ALLYLTRIBUTYLTIN; BINAPHTHYLTHIOPHOSPHORAMIDE; BUTYLTIN DERIVATIVE; DIAMINE DERIVATIVE; DIPHENYLTHIOPHOSPHINIC CHLORIDE; LIGAND; N ETHYL 1,1' BINAPHTHYL 2,2' DIAMINE; PHOSPHINIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; SILVER; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 0043157642     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300099     Document Type: Article

References (28)

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23. Previously we found that this allylation reaction could take place only when the heteroatom on the phosphorus atom was a sulfur atom; if it was an oxygen atom, no reaction could take place. This result strongly suggests that coordination between the sulfur atom and silver metal plays an important role in this reaction. For selected X-ray crystal structures of Cu complexes coordinated by S, N ligands, see: [a] D. M. Koten, D. M. Grove, W. J. Smeets, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1992, 114, 3400-3410. [b] G. R. Brubaker, J. N. Brown, M. K. Yoo, T. M. Kutchan, E. A. Mottel, Inorg. Chem. 1979, 18, 299-302.
24. For chiral ligands with a sulfur atom, see: [a] E. J. Miller, T. B. Brill, A. L. Rheingold, W. C. Fultz, J. Am. Chem. Soc. 1983, 105, 7580-7584. [b] G. Jommi, R. Pagliarin, G. Rizzi, M. Sisti, Synlett 1993, 833-834. [c] Y. Arai, N. Nagata, Y. Masaki, Chem. Pharm. Bull. 1995, 43, 2243-2244. [d] Y. Masaki, Y. Satoh, T. Makihara, M. Shi, Chem. Pharm. Bull. 1996, 44, 454-456. [e] J. Priego, O. G. Mancheno, S. Cabrera, R. G. Arrayas, T. Llamas, J. C. Carretero, Chem. Commun. 2002, 2512-2513 and references cited therein.
25. For chiral ligands with a sulfur atom, see: [a] E. J. Miller, T. B. Brill, A. L. Rheingold, W. C. Fultz, J. Am. Chem. Soc. 1983, 105, 7580-7584. [b] G. Jommi, R. Pagliarin, G. Rizzi, M. Sisti, Synlett 1993, 833-834. [c] Y. Arai, N. Nagata, Y. Masaki, Chem. Pharm. Bull. 1995, 43, 2243-2244. [d] Y. Masaki, Y. Satoh, T. Makihara, M. Shi, Chem. Pharm. Bull. 1996, 44, 454-456. [e] J. Priego, O. G. Mancheno, S. Cabrera, R. G. Arrayas, T. Llamas, J. C. Carretero, Chem. Commun. 2002, 2512-2513 and references cited therein.
26. For chiral ligands with a sulfur atom, see: [a] E. J. Miller, T. B. Brill, A. L. Rheingold, W. C. Fultz, J. Am. Chem. Soc. 1983, 105, 7580-7584. [b] G. Jommi, R. Pagliarin, G. Rizzi, M. Sisti, Synlett 1993, 833-834. [c] Y. Arai, N. Nagata, Y. Masaki, Chem. Pharm. Bull. 1995, 43, 2243-2244. [d] Y. Masaki, Y. Satoh, T. Makihara, M. Shi, Chem. Pharm. Bull. 1996, 44, 454-456. [e] J. Priego, O. G. Mancheno, S. Cabrera, R. G. Arrayas, T. Llamas, J. C. Carretero, Chem. Commun. 2002, 2512-2513 and references cited therein.
27. For chiral ligands with a sulfur atom, see: [a] E. J. Miller, T. B. Brill, A. L. Rheingold, W. C. Fultz, J. Am. Chem. Soc. 1983, 105, 7580-7584. [b] G. Jommi, R. Pagliarin, G. Rizzi, M. Sisti, Synlett 1993, 833-834. [c] Y. Arai, N. Nagata, Y. Masaki, Chem. Pharm. Bull. 1995, 43, 2243-2244. [d] Y. Masaki, Y. Satoh, T. Makihara, M. Shi, Chem. Pharm. Bull. 1996, 44, 454-456. [e] J. Priego, O. G. Mancheno, S. Cabrera, R. G. Arrayas, T. Llamas, J. C. Carretero, Chem. Commun. 2002, 2512-2513 and references cited therein.
28. For chiral ligands with a sulfur atom, see: [a] E. J. Miller, T. B. Brill, A. L. Rheingold, W. C. Fultz, J. Am. Chem. Soc. 1983, 105, 7580-7584. [b] G. Jommi, R. Pagliarin, G. Rizzi, M. Sisti, Synlett 1993, 833-834. [c] Y. Arai, N. Nagata, Y. Masaki, Chem. Pharm. Bull. 1995, 43, 2243-2244. [d] Y. Masaki, Y. Satoh, T. Makihara, M. Shi, Chem. Pharm. Bull. 1996, 44, 454-456. [e] J. Priego, O. G. Mancheno, S. Cabrera, R. G. Arrayas, T. Llamas, J. C. Carretero, Chem. Commun. 2002, 2512-2513 and references cited therein.