Effects of aromatic substituents on binaphthyl-based chiral spiro-type ammonium salts in asymmetric phase-transfer reactions

Advanced Synthesis and Catalysis

Volumn 349, Issue 4-5, 2007, Pages 556-560

  Kano, Taichi ^a   Lan, Quan ^a   Wang, Xisheng ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Alkylation; Amino acids; Asymmetric catalysis; Enantioselectivity; Phase transfer catalysis

Indexed keywords

EID: 34547212920     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600576     Document Type: Article

References (39)

1. For reviews, see: a) B. List, Synlett 2001, 1675;
2. b) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001, 40, 3726;
3. c) M. Movassaghi, E. N. Jacobsen, Science 2002, 298, 1904;
4. d) B. List, Tetrahedron 2002, 58, 5573;
5. e) B. Alcaide, P. Almendros, Angew. Chem. Int. Ed. 2003, 42, 858;
6. f) "Organic Catalysis": Special issue, Adv. Synth. Catal. 2004, 346;
7. g) "Enantioselective Organocatalysis": Special issue, Acc. Chem. Res. 2004, 37;
8. h) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138;
9. i) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719;
10. j) A. Berkessel, H. Gröger, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005.
11. For reviews, see: a) T. Shioiri, in: Handbook of Phase Transfer Catalysis, (Eds.: Y. Sasson, R. Neumann), Blackie Academic & Professional, London, 1997, chap. 14;
12. b) S. Ebrahim, M. Wills, Tetrahedron: Asymmetry 1997, 8, 3163;
13. c) I. A. Esikova, T.S. Nahreini, M.J. O'Donnell, in: Phase-Transfer Catalysis, ACS Symp. Ser. 659, American Chemical Society, Washington, DC, 1997, chap. 7;
14. d) T. Shioiri, A. Ando, M. Masui, T. Miura, T. Tatematsu, A. Bohsako, M. Higashiyama, C. Asakura, in: Phase-Transfer Catalysis, ACS Symp. Ser. 629, American Chemical Society, Washington, DC, 1997, chap. 11;
15. nd edn, (Ed.: I. Ojima), Wiley-VCH, New York, 2000, chap. 10;
16. f) M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3;
17. g) K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013.
18. For representative examples: a) M. J. O'Donnell, S. Wu, J. C Huffman, Tetrahedron 1994, 50, 4507;
19. b) E. J. Corey, F. Xu, M. C Noe, J. Am. Chem. Soc. 1997, 119, 12414;
20. c) S. Arai, Y. Shirai, T. Ishida, T. Shioiri, Chem. Commun. 1999, 49;
21. d) B. Lygo, J. Crosby, J. A. Peterson, Tetrahedron Lett. 1999, 40, 8671;
22. e) F.-Y. Zhang, E. J. Corey, Org. Lett. 2000, 2, 1097;
23. f) Y. N. Belokon, R. G. Davies, M. North, Tetrahedron Lett. 2000, 41, 7245.
24. K. Maruoka, Pure Appl. Chem. 2005, 77, 1285, and references are cited therein.
25. a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519;
26. b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228;
27. c) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. Int. Ed. 2002, 41, 1551;
28. d) T. Ooi, Y. Uematsu, K. Maruoka, Adv. Synth. Catal. 2002, 344, 288;
29. e) T. Ooi, Y. Kubota, K. Maruoka, Synlett 2003, 1931;
30. f) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 5139;
31. g) T. Hashimoto, K. Maruoka, Tetrahedron Lett. 2003, 44, 3313;
32. h) T. Hashimoto, Y. Tanaka, K. Maruoka, Tetrahedron: Asymmetry 2003, 14, 1599.
33. a) T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. Int. Ed. 2002, 41, 4542;
34. b) T. Ooi, M. Kameda, M. Taniguchi, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 9685.
35. 2O (3 equivs.), DMF, 100°C;
36. 2 (6:1), 80°C;
37. 3 (1.5 equivs.), -78°C to room temperature; 1 N HCl, room temperature.
38. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, SIR97, Program for the solution of crystal structures: J. Appl. Crystallogr. 1999, 32, 115.
39. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.