A practical procedure for the removal of the phenylethanol moiety from phenylglycinol-derived lactams

Tetrahedron Asymmetry

Volumn 21, Issue 20, 2010, Pages 2542-2549

  Semak, Vladislav ^a   Escolano, Carmen ^a   Arróniz, Carlos ^a   Bosch, Joan ^a   Amat, Mercedes ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCINE; LACTAM; NITROGEN DERIVATIVE; OXYGEN; PHENETHYL ALCOHOL; PHENYL GROUP; PIPERIDONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COLUMN CHROMATOGRAPHY; DEBENZYLATION; DIASTEREOISOMER; ENANTIOMER; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 78649319940     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.09.014     Document Type: Article

References (61)

1. Chiral nonracemic amino alcohol-derived bicyclic lactams were initially studied by Meyers. For reviews, see: D. Romo, and A.I. Meyers Tetrahedron 47 1991 9503 9569
2. A.I. Meyers, and G.P. Brengel Chem. Commun. 1997 1 8
3. M.D. Groaning, and A.I. Meyers Tetrahedron 56 2000 9843 9873
4. T.C. Coombs, M.D. Lee IV, H. Wong, M. Armstrong, B. Cheng, C. Wenyong, A.F. Moretto, and L.S. Liebeskind J. Org. Chem. 73 2008 882 888
5. For a review on chiral oxazolopiperidone lactams and their role in the synthesis of natural products, see: C. Escolano, M. Amat, and J. Bosch Chem. Eur. J. 12 2006 8198 8207
6. M. Amat, N. Llor, J. Hidalgo, C. Escolano, and J. Bosch J. Org. Chem. 68 2003 1919 1928
7. M. Amat, M. Pérez, N. Llor, C. Escolano, F.J. Luque, E. Molins, and J. Bosch J. Org. Chem. 69 2004 8681 8693
8. M. Amat, M. Pérez, A.T. Minaglia, N. Casamitjana, and J. Bosch Org. Lett. 7 2005 3653 3656
9. M. Amat, C. Escolano, A. Gómez-Esqué, O. Lozano, N. Llor, R. Griera, E. Molins, and J. Bosch Tetrahedron: Asymmetry 17 2006 1581 1588
10. M. Amat, M. Pérez, A.T. Minaglia, B. Peretto, and J. Bosch Tetrahedron 63 2007 5839 5848
11. M. Amat, M. Pérez, A.T. Minaglia, and J. Bosch J. Org. Chem. 73 2008 6920 6923
12. M. Amat, M. Pérez, A.T. Minaglia, D. Passarella, and J. Bosch Tetrahedron: Asymmetry 19 2008 2406 2410
13. M. Amat, M. Pérez, S. Proto, T. Gatti, and J. Bosch Chem. Eur. J. 16 2010 9438 9441
14. M. Amat, V. Elias, N. Llor, F. Subrizi, E. Molins, and J. Bosch Eur. J. Org. Chem. 2010 4017 4026
15. Cleavage of 2-hydroxy-1-phenylethyl moiety from chiral oxazolopyrrolidone lactams derived from (R)-phenylglycinol has been performed by a multistep sequence involving the formation of the corresponding phenylenamide derivative and acid hydrolysis: M.D. Ennis, R.L. Hoffman, N.B. Ghazal, D.W. Old, and P.A. Mooney J. Org. Chem. 61 1996 5813 5817
16. V. Nyzam, C. Belaud, F. Zammattio, and J. Villieras Tetrahedron: Asymmetry 7 1996 1835 1843
17. O. Fains, and J.M. Vernon Tetrahedron Lett. 38 1997 8265 8266
18. S.M. Allin, C.J. Northfield, M.I. Page, and A.M.Z. Slawin Tetrahedron Lett. 40 1999 141 142
19. C. Agami, F. Couty, and G. Evano Tetrahedron Lett. 40 1999 3709 3712
20. J.A. Nieman, and M.D. Ennis Org. Lett. 2 2000 1395 1397
21. R.A. Bragg, J. Clayden, M. Bladon, and O. Ichihara Tetrahedron Lett. 42 2001 3411 3414
22. B. Newhouse, S. Allen, B. Fauber, A.S. Anderson, C.T. Eary, J.D. Hansen, J. Schiro, J.J. Gaudino, E. Laird, D. Chantry, C. Eberhardt, and L.E. Burgess Bioorg. Med. Chem. Lett. 14 2004 5537 5542
23. M.-D. Chen, X. Zhou, M.-Z. He, Y.-P. Ruan, and P.-Q. Huang Tetrahedron 60 2004 1651 1657
24. J.D. Hansen, B.J. Newhouse, S. Allen, A. Anderson, T. Eary, J. Schiro, J. Gaudino, E. Laird, A.C. Allen, D. Chantry, C. Eberhardt, and L.E. Burguess Tetrahedron Lett. 47 2006 69 72
25. Z. Zuo, W. Xie, and D. Ma J. Am. Chem. Soc. 132 2010 13226 13228
26. For other debenzylation methods for amides, see: TFA: R.H. Schlessinger, G.R. Bebernitz, P. Lin, and A.Y. Poss J. Am. Chem. Soc. 107 1985 1777 1778
27. S.J. Shimshock, R.E. Waltermire, and P. Deshong J. Am. Chem. Soc. 113 1991 8791 8796
28. 2, n-BuLi: R.M. Williams, and E. Kwast Tetrahedron Lett. 30 1989 451 454
29. MsOH: S. Paik, and J.Y. Lee Tetrahedron Lett. 47 2006 1813 1815
30. Radical conditions S.R. Baker, A.F. Parsons, and M. Wilson Tetrahedron Lett. 39 1998 331 332
31. p-TsOH: C.-Y. Chern, Y.-P. Huang, and W.M. Kan Tetrahedron Lett. 44 2003 1039 1041
32. D.K. Joshi, J.W. Sutton, S. Carver, and J.P. Blanchard Org. Process Res. Dev. 9 2005 997 1002
33. R.K. Gangopadhyay, and S.K. Das Process Saf. Prog. 27 2008 15 20
34. R. Gigg, and R. Conant J. Chem. Soc., Chem. Commun. 1983 465 466
35. A.A. Haddach, A. Kelleman, and M.V. Deaton-Rewolinski Tetrahedron Lett. 43 2002 399 402
36. M. García-Valverde, R. Pedrosa, and M. Vicente Synlett 2002 2092 2094
37. M. Amat, G. Pshenichnyi, J. Bosch, E. Molins, and C. Miravitlles Tetrahedron: Asymmetry 7 1996 3091 3094
38. M. Amat, J. Bosch, J. Hidalgo, M. Cantó, M. Pérez, N. Llor, E. Molins, C. Miravitlles, M. Orozco, and J. Luque J. Org. Chem. 65 2000 3074 3084 and references therein
39. M. Amat, N. Llor, J. Hidalgo, and J. Bosch Tetrahedron: Asymmetry 8 1997 2237 2240
40. M. Amat, C. Escolano, N. Llor, M. Huguet, M. Pérez, and J. Bosch Tetrahedron: Asymmetry 14 2003 1679 1683
41. See also Ref. 4d
42. M. Amat, O. Lozano, C. Escolano, E. Molins, and J. Bosch J. Org. Chem. 72 2007 4431 4439
43. M. Amat, N. Llor, J. Bosch, and X. Solans Tetrahedron 53 1997 719 730
44. 2O proved fruitless.
45. The use of DMSO as the solvent proved fruitless.
46. J. Santamaria, R. Jroundi, and J. Rigaudy Tetrahedron Lett. 30 1989 4677 4680
47. Refs. 10 and 11 and references therein.
48. When the reaction was carried out in THF the yields were 88% (11) and 12% (17).
49. C.J. Foti, and D.L. Comins J. Org. Chem. 60 1995 2656 2657
50. A. Filippis, D. Gómez Pardo, and J. Cossy Synthesis 2004 2930 2933
51. V.V. Voronenkov, A.N. Vinogradov, and V.A. Belyaev Russ. Chem. Rev. 39 1970 944 952
52. R.H. Crabtree, and A. Habib B.H. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 7 1991 Pergamon Press Oxford 10
53. For examples of the oxidation of enamines with oxygen, see: J.E. Huber Tetrahedron Lett. 9 1968 3271 3272
54. C.S. Foote, A.A. Dzakpasu, and J.W.-P. Lin Tetrahedron Lett. 16 1975 1247 1250
55. H.H. Wasserman, and S. Terao Tetrahedron Lett. 16 1975 1735 1738
56. J. Fetter, K. Lempert, and J. Mølleer Tetrahedron 34 1978 2557 2563
57. N.M. Curtis, A.A. Gorman, and A.L. Prescott J. Am. Chem. Soc 110 1988 7549 7550
58. Y.-G. Chang, and K. Kim Synlett 2002 1423 1426
59. When reaction was performed in MTBE in the presence of a sun lamp for 44 h, the yield and ratio of 11 and 17 were coincident with that described in the Section 5.7.1.
60. R. Kawcki Tetrahedron 57 2001 8385 8390
61. ++1, 91), 248 (100), 130 (89), 104 (58), 91 (51).