Design of a conformationally rigid hydrazide organic catalyst

Advanced Synthesis and Catalysis

Volumn 349, Issue 3, 2007, Pages 441-447

  Lemay, Mathieu ^a   Aumand, Livia ^a   Ogilvie, William W ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Aldehydes; Conformational control; Cycloaddition; Hydrazides; Organic catalysis

Indexed keywords

EID: 34547224498     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600268     Document Type: Article

References (44)

1. a) R. Breslow, Acc. Chem. Res. 1995, 28, 146;
2. b) Y. Murakami, J. Kikuchi, Y. Hiseada, O. Hayashida, Chem. Rev. 1996, 96, 721;
3. c) A. J. Kirby, Angew. Chem. Int. Ed. Engl. 1996, 35, 707;
4. d) N. Gathergood, Australian J. Chem. 2002, 55, 615;
5. e) H. Gröger, J. Wilken, Angew. Chem. Int. Ed. 2001, 40, 529.
6. a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001, 40, 3726;
7. b) B. List, Synlett 2001, 1675;
8. c) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138;
9. d) K. N. Houk, B. List, Acc. Chem. Res. 2004, 37, 487;
10. e) M. L. Clarke, Lett. Org. Chem. 2004, 1, 292;
11. f) W. Notz, R. Tanaka, C F. Barbas, III, Acc. Chem. Res. 2004, 37, 580;
12. g) J. Seayad, B. List, Org. & Biomol. Chem. 2005, 3, 719;
13. h) A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley VCH, Weinheim, 2005.
14. a) B. List, Tetrahedron 2002, 58, 5573;
15. b) M. Movassaghi, E. N. Jacobsen, Science 2002, 298, 1904.
16. For examples, see : a) M. M. Vasbinder, E. R. Jarvo, S. J. Miller, Angew. Chem. Int. Ed. 2001, 40, 2824, and references cited therein;
17. b) P. Vachal, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012, and references cited therein.
18. L. Pignataro, M. Benaglia, R. Annunziata, M. Cinquini, F. Cozzi, J. Org. Chem. 2006, 71, 1458.
19. M. Lemay, W. W. Ogilvie, Org. Lett. 2005, 7, 4141.
20. M. Lemay, W W Ogilvie, J. Org. Chem. 2006, 71, 4663.
21. a) K. A. Ahrendt, C J. Borths, D. W. C MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
22. b) A. B. Northrup, D. W C MacMillan, J. Am. Chem. Soc. 2002, 124, 2458;
23. c) R. M. Wilson, W. S. Jen, D. W. C MacMillan, J. Am. Chem. Soc. 2005, 127, 11616;
24. d) K. Kim, L. S. Hoon; D.-W. Lee, D.-H. Ko, D.-C Ha, Tetrahedron Lett. 2005, 46, 5991;
25. e) K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2005, 127, 10504;
26. f) S. A. Selkälä, A. Sami, A. M. P Koskinen, Eur. J. Org. Chem. 2005, 1620;
27. g) D. C Braddock, I. D. MacGilp, B. G. Perry, Synlett 2003, 1121;
28. h) S. A. Selkälä, J. Tois, P.M. Pihko, A. M. P. Koskinen, Adv. Synth. Catal. 2002, 344, 941;
29. i) R. Gordillo, K. N. Houk, J. Am. Chem. Soc. 2006, 128, 3543.
30. a) C Allemann, R. Gordillo, F. R. Clemente, P. H.-Y Cheong, K.N. Houk, Acc. Chem. Res. 2004, 37, 558;
31. b) R. Gordillo, K. N. Houk, J. Am. Chem. Soc. 2006, 128, 3543.
32. Gaussian 98 (Revision A.9). PM3:
33. a) J. J. P. Stewart, J. Comp. Chem. 1989, 10, 209;
34. b) J. J. P. Stewart, J. Comp. Chem. 1989, 10, 221.
35. Allylic-type strain is also possible between the benzyl side-chain and the iminium moiety but was apparently less significant.
36. I. Fleming, Fronteir Orbitals and Organic Chemical Reactions. Wiley-Interscience, Chichester, 1976.
37. CCDC 610170 and 610171 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data request/cif, or by emailing data request@ccdc.cam. ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44)-1223-336033.
38. Recently the structure of a hydrogen-bonded intermediate was disclosed: R. I. Storer, D. E. Carrera, Y. Ni, D. W. C MacMillan, J. Am. Chem. Soc. 2006, 128, 84.
39. V S. Bryantsev, B. P. Hay, J. Am. Chem. Soc. 2005, 127, 8282.
40. [7]
41. Significant couterion effects have been noted in other organocatalytic cycloadditions, see: a) J. L. Cavill, J.-U Peters, N. C. O. Tomkinson, J. Chem. Soc., Chem. Commun. 2003, 728;
42. [9]
43. P. P. Bart lett, L. H. Knox, Organic Syntheses, Coll. Vol. 5, p. 689.
44. H. Fujioka, N. Kotoku, T. Fujita, R. Inoguchi, K. Murai, Y. Nagatomi, Y. Sawama, Y. Kita Chirality 2003, 15, 60.