Recent developments in the area of asymmetric transfer hydrogenation

Molecules

Volumn 5, Issue 1, 2000, Pages 4-18

  Wills, Martin ^a   Palmer, Matthew ^a   Smith, Athene ^a   Kenny, Jennifer ^a   Walsgrove, Tim ^b  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Asymmetric; Catalysis; Hydrogenation; Ruthenium; Transfer

Indexed keywords

AMINOALCOHOL; KETONE; RUTHENIUM;

ATOMIC PARTICLE; CATALYSIS; ENANTIOMER; HYDROGENATION; METHODOLOGY; REDUCTION; REVIEW;

EID: 0002360918     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/50100004     Document Type: Review

References (27)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons Ltd: NY, 1994.
2. Ojima, I. Catalytic Asymmetric Synthesis; VCH Press: Berlin, 1993.
3. Noyori, R. Chemical multiplication of chirality - science and applications. Chem. Soc. Rev. 1989, 18, 187-208.
4. Noyori, R.; Takaya, H. BINAP - An efficient chiral element for asymmetric catalysis. Acc. Chem. Res. 1990, 23, 345-350.
5. Takaya, H.; Ohno, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, Chapter 1.
6. Noyori, R. Organometallic ways for the multiplication of chirality. Tetrahedron 1994, 50, 4259-4292.
7. Wills, M. in Supplement A3: The chemistry of double-bonded functional groups; Patai, S., Ed.; John Wiley and Sons Ltd, 1997, pp 781-842.
8. Deloux, L.; Srebnik, M. Asymmetric boron-catalyzed reactions. Chem. Rev. 1993, 93, 763-784.
9. Wallbaum, S.; Martens, J. Asymmetric syntheses with chiral oxazaborolidines. Tetrahedron Asymmetry 1992, 3, 1475-1504.
10. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. Practical enantioselective hydrogenation of aromatic ketones. J. Am. Chem. Soc. 1995, 117, 2675-2676.
11. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. Stereoselective hydrogenation of simple ketones catalyzed by Ruthenium(II) complexes. J. Org. Chem. 1996, 61, 4872-4873.
12. Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Asymmetric hydrogenation of cyclic alpha,beta-unsaturated ketones to chiral allylic alcohols. Synlett 1997, 467-469.
13. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. Preferential hydrogenation of aldehydes and ketones. J. Am. Chem. Soc. 1995, 117, 10417-10418.
14. Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Highly enantioselective hydrogenation of simple ketones catalyzed by a Rh-PennPhos complex. Angew. Chem., Int. Edn. Engl. 1998, 37, 1100-1103.
15. A summary of ligands (including our own) which have recently been reported for the asymmetric transfer hydrogenation of ketones are given below. For reasons of space the comparison is limited to the reduction of acetophenone.
16. Palmer, M.; Walsgrove, T.; Wills, M. (1R,2S)-(+)-cis-1-amino-2-indanol: An effective ligand for asymmetric catalysis of transfer hydrogenation of ketones. J. Org. Chem. 1997, 62, 5226-5228.
17. M. Wills and J. Kenny, unpublished results.
18. Noyori, R.; Hashiguchi, S. Asymmetric Transfer Hydrogenation Catalysed by Chiral Ruthenium Complexes. Acc. Chem. Res. 1997, 30, 97-102.
19. Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. The catalyst precursor, catalyst, and intermediate in the Ru-II- promoted asymmetric hydrogen transfer between alcohols and ketones. Angew. Chem., Int. Edn. Engl. 1997, 36, 285-288.
20. M. Wills and A. Smith, unpublished results.
21. Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Synthesis and evaluation of a chiral heterogeneous transfer hydrogenation catalyst. Tetrahedron Asymmetry 1998, 9, 2015-2019.
22. a) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. Asymmetric transfer hydrogenation of imines. J. Am. Chem. Soc. 1996, 118, 4916-4917;
23. b) Wang, G.-Z.; Bäckvall, J.-E. Ruthenium-catalyzed transfer hydrogenation of imines by propan- 2-ol. J. Chem. Soc., Chem. Commun. 1992, 980-982;
24. c) Ahn, K. H.; Ham, C.; Kim S.-K.; Cho, C.-W. Practical synthesis of chiral sultam auxiliaries: 3-substituted 1,2-benzisothiazoline 1,1-dioxides. J. Org. Chem. 1997, 62, 7047-7048.
25. a) ter Halle, R.; Schulz, E.; Lemaire, M. Heterogeneous enentioselective catalytic reduction of ketones. Synlett 1997, 1257-1258;
26. b) Breysse, E.; Pinel, C.; Lemaire, M. Use of heterogenized dialdimine ligands in asymmetric transfer hydrogenation. Tetrahedron Asymmetry 1998, 9, 897-900.
27. Hashiguchi, S.; Fujii, A.; Haack, K.-J.; Matsumura, K.; Ikariya, T.; Noyori, R. Kinetic resolution of racemis secondary alcohols by Ru(II)-catalysed hydrogen transfer. Angew. Chem. Int. Ed. Engl. 1997, 36, 288-290.