The phosphate-carboxylate mixed-anhydride method: A mild, efficient process for ester and amide bond construction

Tetrahedron

Volumn 68, Issue 27-28, 2012, Pages 5415-5421

  McNulty, James ^a   Vemula, Ramesh ^a   Krishnamoorthy, Venkatesan ^a   Robertson, Al ^b  

^a MCMASTER UNIVERSITY   (Canada)

^b Cytec Canada Inc   (Canada)

Author keywords

Acylation; Amide; Chiral amines; Ester; Mixed anhydride; Organocatalysis

Indexed keywords

ALPHA AMINO ACID; AMIDE; CARBOXYL GROUP; CARBOXYLIC ACID; ESTER; PHOSPHATE;

ACYLATION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; ESTERIFICATION; PRIORITY JOURNAL; STOICHIOMETRY; SYNTHESIS;

EID: 84862010010     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.04.103     Document Type: Article

References (48)

1. J. Otera Esterification Methods, Reactions and Applications 2003 Wiley VCH Weinheim 301-312
2. M.B. Smith, and J. March Advanced Organic Chemistry 5th ed. 2001 Wiley New York, NY pp 484-490
3. C. Larock Comprehensive Organic Transformations 2nd ed. 1999 Wiley-VCH New York, NY pp 1932-1941
4. G. Mehta Synthesis 1972 262 268
5. J. McNulty, S. Cheekoori, J.J. Nair, V. Larichev, A. Capretta, and A.J. Robertson Tetrahedron Lett. 46 2005 3641 3644
6. O. Mitsunobu, and M. Yamada Bull. Chem. Soc. Jpn. 40 1967 2380 2382
7. R. Dembinski Eur. J. Org. Chem. 2004 2763 2772
8. J. Inanga, K. Hirata, H. Saeki, T. Katsuki, and M. Yamaguchi Bull. Chem. Soc. Jpn. 52 1979 1989 1993
9. H.J. Liu, W.H. Chan, and S.P. Lee Tetrahedron Lett. 19 1978 4461 4464
10. A.K. Adak Synlett 2004 1651 1652
11. H.J. Liu, and S.I. Sabesan Can. J. Chem. 58 1980 1645 2648
12. T. Kaiho, S. Masamune, and T. Toyoda J. Org. Chem. 47 1982 1612 1614
13. A. Parenty, X. Moreau, and J.M. Campagne Chem. Rev. 106 2006 911 939
14. J. McNulty, J.J. Nair, S. Cheekoori, V. Larichev, A. Capretta, and A.J. Robertson Chem. - Eur. J. 12 2006 9314 9322
15. J. Dyck, S. Zavorine, J. McNulty, A. Capretta, A.J. Robertson, and V. Larichev J. Organomet. Chem. 690 2005 2548 2552
16. J. McNulty, A. Capretta, A.J. Robertson, V. Larichev, and J. Dyck Angew. Chem., Int. Ed. 42 2003 4051 4054
17. J. McNulty, A. Capretta, A.J. Robertson, V. Larichev, and J. Dyck J. Org. Chem. 68 2003 1597 1600
18. J. McNulty, V. Krishnamoorthy, and A. Robertson Tetrahedron Lett. 49 2008 6344 6347
19. J.E. Won, H.K. Kim, J.J. Kim, H.S. Yim, M.J. Kim, S.B. Kang, H.A. Chung, S.G. Lee, and Y.J. Yoon Tetrahedron 63 2007 12720 12730
20. M. Hikota, H. Tone, K. Horita, and O. Yonemitsu J. Org. Chem. 55 1990 7 9
21. S. Nahm, and S.M. Weinreb Tetrahedron Lett. 22 1982 3815 3818
22. J. McNulty, V. Grunner, and J. Mao Tetrahedron Lett. 42 2001 5609 5612
23. F. Giacalone, M. Gruttadauria, P. Agrigento, and R. Noto Chem. Soc. Rev. 41 2012 2406 2447
24. C. Lindner, R. Tandon, Y. Liu, B. Maryasin, and H. Zipse Org. Biomol. Chem. 2012 10.1039/c2ob07058h
25. A.G.M. Barrett, A.S. Cook, and A. Kamimura Chem. Commun. 1998 2533 2534
26. O. Cervinka, and O. Kriz Collect. Czech. Chem. Commun. 38 1973 938 942
27. M.J. Liley, T. Johnson, and S.E. Gibson J. Org. Chem. 71 2006 1322 1329
28. Y.-Q. Cao, G.-Q. Wu, Y.-B. Li, Z. Dai, and B.-H. Chen Synth. Commun. 36 2006 3353 3358
29. M. Armstrong, and J.E. Copenhaver J. Am. Chem. Soc. 65 1943 2252 2253
30. R. Qiu, G. Zhang, X. Ren, X. Xu, R. Yang, S. Luo, and S. Yin J. Organomet. Chem. 695 2010 1182
31. T. Sato, S. Kawasaki, N. Oda, S. Yagi, S.A.A. El Bialy, J. Uenishi, M. Yamauchi, and M. Ikeda J. Chem. Soc., Perkin Trans. 1 2001 2623 2631
32. J.-J. Kim, Y.-D. Park, D.-H. Kweon, Y.-J. Kang, H.-K. Kim, S.-G. Lee, S.-D. Cho, W.-S. Lee, and Y.-J. Yoon Bull. Korean Chem. Soc. 25 2004 501 505
33. C. Bourne, S. Roy, J.L. Wiley, B.R. Martin, B.F. Thomas, A. Mahadevan, and R.K. Razdan Bioorg. Med. Chem. 15 2007 7850 7864
34. E.R. Murphy, J.R. Martinelli, N. Zaborenko, S.L. Buchwald, and K.F. Jensen Angew. Chem., Int. Ed. 46 2007 1734 1737
35. M. Ihara, M. Takahashi, N. Taniguchi, K. Yasui, K. Fukumoto, and T. Kametani J. Chem. Soc., Perkin Trans. 1 1989 897 903
36. K. Ishihara, M. Kubota, H. Kurihara, and H. Yamamoto J. Org. Chem. 61 1996 4560 4567
37. K. Sisido, K. Kumazawa, and H. Nozaki J. Am. Chem. Soc. 82 1960 125 129
38. A.K. Chakraborti, and Shivani J. Org. Chem. 71 2006 5785 5788
39. J.M. McIntosh, R. Thangarasa, N.K. Foley, D.J. Ager, D.E. Froen, and R.C. Klix Tetrahedron 50 1994 1967 1974
40. M. Szlosek, X. Franck, B. Figadere, and A. Cave J. Org. Chem. 63 1998 5169 5172
41. E.M. Jarho, J.I. Venalainen, S. Poutiainen, H. Leskinen, J. Vepsalainen, J.A.M. Christiaans, M.M. Forsberg, P.T. Mannisto, and E.A.A. Wallen Bioorg. Med. Chem. 15 2007 2024 2031
42. T. Mimoto, N. Hattori, H. Takaku, S. Kisanuki, T. Fukazawa, K. Terashima, R. Kato, S. Nojima, S. Misawa, T. Ueno, J. Imai, H. Enomoto, S. Tanaka, H. Sakikawa, M. Shintani, H. Hayashi, and Y. Kiso Chem. Pharm. Bull. 48 2000 1310 1326
43. K. Kawasaki, K. Hirase, M. Miyano, T. Tsuji, and M. Iwamoto Chem. Pharm. Bull. 40 1992 3253 3260
44. Y. Hayashi, T. Tamura, and M. Shoji Adv. Synth. Catal. 346 2004 1106 1110
45. T. Mukaiyama, S. Kobayashi, and T. Sanu Tetrahedron 46 1990 4653 4662
46. T. Mukaiyama, N. Iwasawa, R.W. Stevens, and T. Haga Tetrahedron 40 1984 1381 1390
47. N. Iwasa, and T. Mukaiyama Chem. Lett. 1982 1441 1444
48. J. Ichikawa, M. Asami, and T. Mukaiyama Chem. Lett. 1984 949 952