3486
A. Bisai, V.K. Singh / Tetrahedron 68 (2012) 3480e3486
18. (a) For a preliminary communication of this work, see; Bisai, A.; Singh, V. K. Org.
Lett. 2006, 8, 2405; (b) For a review, see; Singh, P. K.; Singh, V. K. Pure Appl.
Chem. 2010, 82, 1845.
19. Aschwanden, P.; Stephenson, C. R. J.; Carreira, E. M. Org. Lett. 2006, 8, 2437.
20. Rosa, J. N.; Santos, A. G.; Afonso, C. A. M. J. Mol. Catal. A: Chem. 2004, 214, 161.
21. (a) Weissberg, A.; Halak, B.; Portnoy, M. J. Org. Chem. 2005, 70, 4556; (b) Zeng,
T.; Yang, L.; Hudson, R.; Song, G.; Moores, A. R.; Li, C.-J. Org. Lett. 2011, 13, 442.
22. (a) Chin, J. W.; Cropp, T. A.; Anderson, J. C.; Mukherji, M.; Zhang, Z.; Schultz, P. G.
Science 2003, 301, 964; (b) Wang, L.; Schultz, P. G. Angew. Chem., Int. Ed. 2004, 44,
34; (c) Cropp, T. A.; Schultz, P. G. Trends Genet. 2004, 20, 625.
Chiralpak AD-H (4.6 cm I.D.ꢂ25 cm), 80:20 hexanes/i-PrOH,
1.0 mL/min flow rate,
l
¼254 nm, tR (major)¼15.33 min and tR
(minor)¼13.21 min; 1H NMR (CDCl3, 400 MHz)
: 7.62 (d, J¼7.8 Hz,
d
1H), 7.38 (d, J¼8.5 Hz, 2H), 7.22 (d, J¼8.3 Hz, 2H), 7.04 (m, 2H), 6.76
(dd, J¼32.2, 8.8 Hz,1H); 5.43 (s,1H), 3.73 (s, 3H), 2.41 (s, 3H), 2.32 (s,
3H). Anal. Calcd for C24H22BrNO: C, 68.58; H, 5.28; N, 3.33. Found: C,
68.69; H, 5.27; N, 3.34.
23. (a) Scott, J. W. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley:
New York, NY, 1989; Vol. 19, p 209; (b) Kaptain, B.; Boesten, W. H. J.; Broxter-
mann, Q. B.; Peters, P. J. H.; Schoemaker, H. E.; Kamphuis, J. Tetrahedron:
Asymmetry 1993, 4, 1113.
5.3. General experimental procedure for the catalytic
asymmetric alkynylation of a-imino ester
24. (a) Rossen, K. Angew. Chem., Int. Ed. 2001, 40, 4611; (b) Noyori, R.; Ohkuma, T.
Angew. Chem., Int. Ed. 2001, 40, 40; (c) Burk, M. J. Acc. Chem. Res. 2000, 33, 363.
25. (a) Pena, D.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Org.
Lett. 2003, 4, 475; (b) Evans, D. A.; Michael, F. E.; Tedrow, J. S.; Campos, K. R.
J. Am. Chem. Soc. 2003, 125, 3534.
The procedure was same as one-pot three-component synthesis
of (R) propargylamines except Cu(II)OTf and ethylglyoxylate were
used instead of Cu(I)PF6 and aromatic aldehydes, respectively.
26. Ji, J.-X.; Xu, J.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11196.
27. Combs, T. L. PCT Int. Appl., 2003, WO 2003/087036; Chem. Abstr. 139, 308017.
28. Kamble, R. K.; Singh, V. K. Tetrahedron Lett. 2003, 44, 5347.
29. Kauffman, G. S.; Harris, G. D.; Dorow, R. L.; Stone, B. R. P.; Parsons, R. L., Jr.; Pesti,
J. A.; Magnus, N. A.; Fortunak, J. M.; Confalone, P. N.; Nugent, W. A. Org. Lett.
2000, 2, 3119.
Acknowledgements
V.K.S. thanks the DST, India for a research grant through J.C. Bose
fellowship. A.B. thanks the CSIR, New Delhi for a Senior Research
Fellowship.
30. Shilov, A. E.; Shul’pin, G. B. Chem. Rev. 1997, 97, 2879.
31. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, NY, 1994.
32. (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10,
846; (b) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57,
4306.
Supplementary data
33. Nagashimha, H.; Ueda, T.; Nishiyama, H.; Itoh, K. Chem. Lett. 1993, 347.
34. Nishiyama, H.; Tajima, T.; Takayama, M.; Itoh, K. Tetrahedron: Asymmetry 1993,
4, 1461.
35. (a) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc.
1994, 116, 2223; (b) Doyle, M. P.; Petersom, C. S.; Zhou, Q.-L.; Nagashimha, H.
Chem. Commun. 1997, 951.
Selected 1H and 13C data of the synthesized compounds. Sup-
plementary data associated with this article can be found in online
36. (a) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814;
(b) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119,
10859.
References and notes
37. (a) Evans, D. A.; Murry, J. A.; Von Matt, P.; Norcross, R. D.; Miller, S. J. Angew.
Chem., Int. Ed. Engl. 1995, 34, 798; (b) Davies, I. W.; Gerena, L.; Cai, D.; Larsen, R.
D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145.
38. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K.
Organometallics 1989, 8, 846.
39. For some applications of i-Pr-pybox 1b in enantioselective reactions, see: (a)
Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325; (b) Sammis, G. M.;
Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928; (c) Fischer, C.; Fu, G.
C. J. Am. Chem. Soc. 2005, 127, 4594; (d) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc.
2005, 127, 10482 and references cited therein.
40. (a) DattaGupta, A.; Bhuniya, D.; Singh, V. K. Tetrahedron 1994, 50, 13725;
(b) Ginotra, S.; Singh, V. K. Org. Biomol. Chem. 2006, 4, 4370; (c) Ginotra, S.;
Singh, V. K. Tetrahedron 2006, 62, 3573; (d) Sekar, G.; DattaGupta, A.; Singh, V.
K. J. Org. Chem. 1998, 63, 2961; (e) DattaGupta, A.; Singh, V. K. Tetrahedron Lett.
1996, 37, 2633.
41. (a) Lu, J.; Ji, S.-J.; Teo, Y.-C.; Loh, T.-P. Org. Lett. 2005, 7, 159; (b) Lu, J.; Ji, S.-J.; Loh,
T.-P. Chem. Commun. 2005, 2345; (c) Lu, J.; Hong, M. L.; Ji, S.-J.; Teo, Y. C.; Loh, T.
P. Chem. Commun. 2005, 4217; (d) Lu, J.; Ji, S. J.; Teo, Y.-C.; Loh, T.-P. Tetrahedron
Lett. 2005, 46, 7435.
1. (a) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem.
1995, 60, 1590; (b) Yu, P. H.; Davis, B. A.; Bouton, A. A. J. Med. Chem. 1992, 35,
3705.
2. Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. J. Am.
Chem. Soc. 1990, 112, 3715.
€
3. (a) Mecozzi, T.; Petrini, M. J. Org. Chem. 1999, 64, 8970; (b) Franz, D. E.; Fassler,
R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245; (c) Carreira, E. M.; Franz, D.
E.; Fassler, R.; Tomooka, C. S. Acc. Chem. Res. 2000, 33, 373; (d) Mahrwald, R.;
Quint, S. Tetrahedron Lett. 2001, 42, 1655; (e) Carriera, E. M. Chimia 2001, 55,
818; (f) Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2003, 44, 4171;
(g) Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. Angew. Chem., Int. Ed. 2003, 42,
4244.
4. (a) Marshall, J. A.; Wolf, M. A. J. Org. Chem. 1996, 61, 3238; (b) Poerwono, H.;
Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711; (c) Rae, A.; Ker, J.;
Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561.
5. (a) Bloch, R. Chem. Rev. 1998, 98, 1407; (b) Enders, D.; Reinhold, U. Tetrahedron:
Asymmetry 1997, 8, 1895.
6. (a) Mori, Y.; Hayashi, H. Tetrahedron 2000, 58, 1789; (b) Galliford, C. V.; Beenen,
M. A.; Nguyen, S. T.; Scheidt, K. A. Org. Lett. 2003, 5, 3487; (c) Garcia, C. I.;
Tillack, A.; Hartung, C. G.; Beller, M. Tetrahedron Lett. 2003, 44, 3217.
7. (a) Takahashi, T.; Bao, F.; Gao, G.; Ogasawara, M. Org. Lett. 2003, 5, 3479;
(b) Qian, M.; Negishi, E. Org. Process Res. Dev. 2003, 7, 412.
42. (a) Singh, P. K.; Singh, V. K. Org. Lett. 2008, 10, 4121; (b) Singh, P. K.; Singh, V. K.
Org. Lett. 2010, 12, 80.
43. For use of PMPNH2 and their removal under oxidative cleavage, see; (a) Cordova,
ꢁ
A.; Notz, W.; Zhong, G.; Betancort, M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124,
1842; (b) Enders, D.; Grondal, C.; Vrettou, M.; Raabe, G. Angew. Chem., Int. Ed.
2005, 44, 4079; (c) For removal of o-anisidyl group under oxidative condition,
see; Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc.
2001, 123, 10409.
8. Tuulmets, A.; Pallin, V.; Tammiku-Taul, J.; Burk, P.; Raie, K. J. Phys. Org. Chem.
2002, 15, 701.
9. (a) Harada, T.; Fujiwara, T.; Iwazaki, K.; Oku, A. Org. Lett. 2000, 2, 1855;
(b) Rosas, N.; Sharma, P.; Alvarez, C.; Gomez, E.; Gutierrez, Y.; Mendez, M.;
Toscano, R. A.; Maldonado, L. A. Tetrahedron Lett. 2003, 44, 8019.
10. Akullian, L. C.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 5971.
11. (a) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638; (b) Wei, C.; Mague, J. T.; Li,
C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5749; (c) For a review, see: Wei, C.; Li,
Z.; Li, C.-J. Synlett 2004, 1472.
44. (a) Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806; (b)
Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
45. Beckwith, A. L. J.; Zavitas, A. A. J. Am. Chem. Soc. 1986, 108, 8230 and references
cited therein.
46. Fora reviewon the p-stackingeffect in asymmetric synthesis, see: (a) Jones, G. B.;
12. (a) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed.
2003, 42, 5763; (b) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed.
2002, 41, 2535; (c) Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem.
Eur. J. 2003, 9, 2997; (d) Gommermann, N.; Knochel, P. Chem. Commun. 2004,
2324; (e) Gommermann, N.; Knochel, P. Chem. Commun. 2005, 4175.
13. Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2003, 5, 3273.
14. (a) Benaglia, M.; Negri, D.; Dell’Anna, G. Tetrahedron Lett. 2004, 45, 8705;
(b) Orlandi, S.; Colombo, F.; Benaglia, M. Synthesis 2005, 1689; (c) Colombo, F.;
Benaglia, M.; Orlandi, S.; Usuelli, F.; Celentano, G. J. Org. Chem. 2006, 71, 2064.
Chapman, B. J. Synthesis 1995, 475; (b) Meyer, E. A.; Castellano, R. K.; Diederich, F.
Angew. Chem., Int. Ed. 2003, 42, 1210.
47. For CH/p interaction between aromatic ring and aliphatic CeH atom, see: (a)
Dreos, R.; Geremia, S.; Nardin, G.; Randaccio, L.; Tauzher, G.; Vuano, S. Inorg.
Chim. Acta 1998, 272, 74; (b) Mandal, D.; Gupta, B. D. Organometallics 2006, 25,
3305.
48. (a) Enzyme Inhibitors as Drugs; Sandler, M., Ed.; The MacMillan Ltd.: London,
1980; (b) Abdulganeeva, S. A.; Erzhanov, K. B. Russ. Chem. Rev. 1991, 60, 676; (c)
Angst, C. Pure Appl. Chem. 1987, 59, 373.
€
15. Knopfel, T. F.; Aschwanden, P.; Ichikawa, T.; Watanabe, T.; Carreira, E. M. Angew.
49. (a) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal.
2004, 346, 42; (b) Shao, Z.; Wang, J.; Ding, K.; Chan, A. S. C. Adv. Synth. Catal.
2007, 349, 2375; (c) Wang, J.; Shao, Z.; Yu, K. D. W. Y.; Chan, A. S. C. Adv. Synth.
Catal. 2009, 351, 1250.
Chem., Int. Ed. 2004, 43, 5971.
16. Jiang, B.; Si, Y.-G. Angew. Chem., Int. Ed. 2004, 43, 216.
17. (a) Wu, T. R.; Chong, J. M. Org. Lett. 2006, 8, 15; (b) Vorogushin, A. V.; Predeus, A.
V.; Wulff, W. D.; Hansen, H. J. J. Org. Chem. 2003, 68, 5826.