Enantioselective benzoin condensation catalyzed by bifunctional N-heterocyclic carbenes

Chinese Science Bulletin

Volumn 55, Issue 17, 2010, Pages 1753-1757

  Huang, Xue Liang ^a   Ye, Song ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

hydroxyketones; Asymmetric catalysis; Benzoin condensation; Bifunctional N heterocyclic carbene

Indexed keywords

EID: 77953881172     PISSN: 10016538     EISSN: 18619541     Source Type: Journal    
DOI: 10.1007/s11434-010-3122-7     Document Type: Article

References (34)

1. Hanessian S. Total Synthesis of Natural Products: The "Chironr" Approach. Pergamon: Oxford, 1983. Chapter 2.
2. Tanaka T, Kawase M, Tani S. α-Hydroxyketones as inhibitiors of urease. Bioorg Med Chem, 2004, 12: 501-505.
3. Vedejs E. Method for direct hydroxylation of enolates. Transition metal peroxide reactions. J Am Chem Soc, 1973, 96: 5944-5946.
4. Davis F A, Chen B C. Asymmetric hydroxylation of enolates with N-sulfonyloxaziridines. Chem Rev, 1992, 92: 919-934.
5. Horiuchi C A, Takeda A, Chai W, et al. A novel synthesis of α-hydroxy- and α,α′-dihydroxyketone from α-iodo and α,α′-diiodo ketone using photoirradiation. Tetrahedron Lett, 2003, 44: 9307-9311.
6. Satao S, Takahashi R, Sodesawa D, et al. Synthesis of α-hydroxyketones from 1, 2-diols over Cu-based catalyst. Catal Commun, 2005, 6: 607-610.
7. Bøevig A, Sundén A, Córdova A. Direct catalytic enantioselective α-aminoxylation of ketones: A stereoselective synthesis. Angew Chem Int Ed, 2004, 43: 1109-1112.
8. Hayashi Y, Yamaguchi J, Sumiya T, et al. Direct proline-catalyzed asymmetric α-aminoxylation of ketones. Angew Chem Int Ed, 2004, 43: 1112-1115.
9. Okada H, Mori T, Saikawa Y, et al. Formation of α-hydroxyketones via irregular Wittig reaction. Tetrahedron Lett, 2009, 50: 1276-1278.
10. Sheehan J, Hunnemann D H. Homogeneous asymmetric catalysis. J Am Chem Soc, 1966, 88: 3666-3667.
11. Enders D, Balensiefer T. Nucleophilic carbenes in asymmetric organocatalysis. Acc Chem Res, 2004, 37: 534-541.
12. Marion N, Diez-Gonzalez S, Nolan S P. N-heterocyclic carbenes as organocatalysts. Angew Chem Int Ed, 2007, 46: 2988-3000.
13. Enders D, Niemeier O, Henseler A. Organocatalysis by N-heterocyclic carbenes. Chem Rev, 2007, 107: 5606-5655.
14. Sheehan J, Hara T. Asymmetric thiazolium salt catalysis of the benzoin condensation. J Org Chem, 1974, 39: 1196-1199.
15. Dvorak C A, Raval V H. Catalysis of benzoin condensation of by conformationally restricted chiral bicyclic thiazolium salts. Tetrahedron Lett, 1998, 39: 2925-2928.
16. Tagaki W, Tamura Y. Asymmetric benzoin condensation catalyzed optically active thiazolium salts in micellar two-phase media. Bull Chem Soc Jpn, 1980, 53: 478-480.
17. Zhao C, Chen S, Wu P, et al. Asymmetric benzoin condensation catalyzed by optically active micellar thiazolium salts. Huaxue Xuebao, 1988, 46: 784-790.
18. Marti J, Castells J, Lopez Calahorra F. Introduction to a rational design of chiral thiazolium salts. Tetrahedron Lett, 1993, 34: 521-524.
19. Enders D, Breuer K, Teles J H. A novel asymmetric benzoin reaction catalyzed by chiral triazolium salt. Helv Chim Acta, 1996, 79: 1217-1221.
20. Enders D, Kallfass U. An efficient nucleophilic carbene catalyst for the asymmetric benzoin condensation. Angew Chem Int Ed, 2002, 41: 1743-1745.
21. Ma Y, Wei S, Wu J, et al. From mono-triazolium salt to bis-triazolium salt: Improvement of the asymmetric intermolecular benzoin condensation. Adv Synth Catal, 2008, 350: 2645-2651.
22. Zhang Y R, He L, Wu X, et al. Chiral N-heterocyclic carbene catalyzed staudinger reaction of ketenes with imines. Org Lett, 2008, 10: 277-280.
23. He L, Lv H, Zhang Y R, et al. Formal cycloaddition of disubstituted ketenes with 2-oxoaldehydes catalyzed by chiral N-heterocyclic carbenes. J Org Chem, 2008, 73: 8101-8103.
24. Zhang Y R, Lv H, Zhou D, et al. Chiral N-heterocyclic carbenecatalyzed formal [4+2] cycloaddition of ketenes with enones: Highly enantioselective synthesis of trans- and cis-δ-lactones. Chem Eur J, 2008, 14: 8473-8476.
25. Huang X L, He L, Shao P L, et al. [4+2] cycloaddition of ketenes with N-benzoyldiazenes catalyzed by N-heterocyclic carbenes. Angew Chem Int Ed, 2009, 48: 192-195.
26. Enders D, Han J. Synthesis of enantiopure triazolium salts from pyroglutamic acid and their evaluation in the benzoin condensation. Tetrahedron: Asymmetry, 2008, 19: 1367-1371.
27. Saito S, Yamamoto H. Design of acid-base catalysis for the asymmetric direct aldol reaction. Acc Chem Res, 2004, 37: 570-579.
28. Ikariya T, Blacker A J. Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts. Acc Chem Res, 2007, 40: 1300-1308.
29. Doyle A G, Jacobsen E N. Small-molecule H-bond donors in asymmetric catalysis. Chem Rev, 2007, 107: 5713-5743.
30. Davie E A C, Mennen S M, Xu Y, et al. Asymmetric catalysis mediated by synthetic peptides. Chem Rev, 2007, 107: 5759-5812.
31. Paull D H, Abraham C J, Scerba M T, et al. Bifunctional asymmetric catalysis: Cooperative Lewis acid/base systems. Acc Chem Res, 2008, 41: 655-663.
32. He L, Zhang Y R, Huang X L, et al. Chiral bifunctional N-heterocyclic carbenes: Synthesis and application in the aza-Morita-Baylis-Hillman reaction. Synthesis, 2008, 17: 2825-2829.
33. Lv H, Zhang Y R, Huang X L, et al. Asymmetric dimerization of disubstituted ketenes catalyzed by N-heterocyclic carbenes. Adv Synth Catal, 2008, 350: 2715-2718.
34. Demer A S, Şeşenoglu Ö, Eren E, et al. Enantioselective synthesis of α-hydroxy ketones via benzaldehyde Lyase-catalyzed C-C bond formation reaction. Adv Synth Catal, 2002, 344: 96-103.