Trihaloacetaldehyde N,O-acetals: useful building blocks for dihalomethylene compounds

Tetrahedron

Volumn 66, Issue 25, 2010, Pages 4530-4541

  Yanai, Hikaru ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

, Dihaloketone; Dechlorination; Defluorinative alkylation; One pot synthesis; Reformatsky reaction

Indexed keywords

ACETAL DERIVATIVE; ALKYLLITHIUM DERIVATIVE; ALPHA,ALPHA DIFLUOROKETONE; CARBENE; DIHALOMETHYLENE DERIVATIVE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; TRIFLUOROACETALDEHYDE N,O ACETAL DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; PRIORITY JOURNAL; TEMPERATURE MEASUREMENT;

EID: 77953123661     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.061     Document Type: Article

References (71)

1. In: Ojima I. (Ed). Fluorine in Medicinal Chemistry and Chemical Biology (2009), Wiley-Blackwell, Oxford, UK
2. Bégué J.-P., and Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine (2008), Wiley, New York, NY, USA
3. In: Welch J.T., and Eswarakrishnan S. (Eds). Fluorine in Bioorganic Chemistry (1991), Wiley, New York, NY
4. In: Filler R., and Kobayashi Y. (Eds). Biomedicinal Aspects of Fluorine Chemistry (1982), Elsevier, Amsterdam
5. Hertel L.W., Boder G.B., Kroin J.S., Rinzel S.M., Poore G.A., Todd G.C., and Grindey G.B. Cancer Res. 50 (1990) 4417-4422
6. Szarek M.A., Wu X., and Szarek W.A. Carbohydr. Res. 299 (1997) 165-170
7. Wang R.-W., Qiu X.-L., Bols M., Ortega-Caballero F., and Qing F.-L. J. Med. Chem. 49 (2006) 2989-2997
8. Halazy S., Ehrhard A., and Danzin C. J. Am. Chem. Soc. 113 (1991) 315-317
9. Hikishima S., Isobe M., Koyanagi S., Soeda S., Shimeno H., Shibuya S., and Yokomatsu T. Bioorg. Med. Chem. 14 (2006) 1660-1670
10. Schirlin D., Baltzer S., Van Dorsselaer V., Weber F., Weill C., Altenburger J.M., Neises B., Flynn G., Remy J.M., and Tarnus C. Bioorg. Med. Chem. Lett. 3 (1993) 253-258
11. Schirlin D., van Dorsselaer V., Tarnus C., Taylor D.L., Tyms A.S., Baltzer S., Weber F., Remy J.M., Brennan T., Farr R., and Janowick D. Bioorg. Med. Chem. Lett. 4 (1994) 241-246
12. Sham H.L., Wideburg N.E., Spanton S.G., Kohlbrenner W.E., Betebenner D.A., Kempf D.J., Norbeck D.W., Plattner J.J., and Erickson J.W.J. Chem. Soc., Chem. Commun. (1991) 110-112
13. Silva A.M., Cachau R.E., Sham H.L., and Erickson J.W. J. Mol. Biol. 255 (1996) 321-346
14. Skiles J.W., Miao C., Sorek R., Jacober S., Mui P.W., Chow G., Weldon S.M., Possanza G., Skoog M., Keirns J., Letts G., and Rosenthal A.S. J. Med. Chem. 35 (1992) 4795-4808
15. Doherty A.M., Sircar I., Kornberg B.E., Quin J., Winters R.T., Kaltenbronn J.S., Taylor M.D., Batley B.L., Rapundalo S.R., Ryan M.J., and Painchaud C.A. J. Med. Chem. 35 (1992) 2-14
16. Schirlin D., Tarnus C., Baltzer S., and Remy J.M. Bioorg. Med. Chem. Lett. 2 (1992) 651-654
17. Eda M., Ashimori A., Akahoshi F., Yoshimura T., Inoue Y., Fukaya C., Nakajima M., Fukuyama H., Imada T., and Nakamura N. Bioorg. Med. Chem. Lett. 8 (1998) 913-918
18. Eda M., Ashimori A., Akahoshi F., Yoshimura T., Inoue Y., Fukaya C., Nakajima M., Fukuyama H., Imada T., and Nakamura M. Bioorg. Med. Chem. Lett. 8 (1998) 919-924
19. Akahoshi F., Ashimori A., Sakashita H., Yoshimura T., Eda M., Imada T., Nakajima M., Mitsutomi N., Kuwahara S., Ohtsuka T., Fukaya C., Miyazaki M., and Nakamura N. J. Med. Chem. 44 (2001) 1297-1304
20. Gerth K., Steinmetz H., Höfle G., and Jansen R. Angew. Chem., Int. Ed. 47 (2008) 600-602
21. Teruya T., Nakagawa S., Koyama T., Arimoto H., Kita M., and Uemura D. Tetrahedron 60 (2004) 6989-6993
22. Gao S., Wang Q., and Chen C. J. Am. Chem. Soc. 131 (2009) 1410-1412
23. Larsen T.O., and Breinholt J. J. Nat. Prod. 62 (1999) 1182-1184
24. Fu X., Ferreira M.L.G., Schmitz F.J., and Kelly-Borges M. J. Nat. Prod. 61 (1998) 1226-1231
25. Luknitskii F.I. Chem. Rev. 75 (1975) 259-289
26. Ishii A., and Takeda Y. Yuki Gosei Kagaku Kyokaishi 57 (1999) 898-900
27. Braid M., Iserson H., and Lawlor F.E. J. Am. Chem. Soc. 76 (1954) 4027-4029
28. Mikami K., Itoh Y., and Yamanaka M. Chem. Rev. 104 (2004) 1-16
29. Mikami K., Yajima T., Takasaki T., Matsukawa S., Terada M., Uchimaru T., and Maruta M. Tetrahedron 52 (1996) 85-98
30. Torii H., Nakadai M., Ishihara K., Saito S., and Yamamoto H. Angew. Chem., Int. Ed. 43 (2004) 1983-1986
31. Yanai H., Mimura H., Kawada K., and Taguchi T. Tetrahedron 63 (2007) 2153-2160
32. Bégué J.-P., Bonnet-Delpon D., Crousse B., and Legros J. Chem. Soc. Rev. 34 (2005) 562-572
33. Billard T., Gille S., Ferry A., Barthelemy A., Christophe C., and Langlois B.R. J. Fluorine Chem. 126 (2005) 189-196
34. Loh T.-P., and Li X.-R. Chem. Commun. (1996) 1929-1930
35. Funabiki K., Nojiri M., Matsui M., and Shibata K. Chem. Commun. (1998) 2051-2052
36. For dichloroketene acetals, see:
37. Guseva S.A., Mirskova A.N., Levkovskaya G.G., Kalikhman I.D., and Voronkov M.G. Zh. Org. Khim. 24 (1988) 298-307
38. J. Org. Chem. USSR 24 (1988) 261-268
39. Mamedov S., and Lerner G. Zh. Obshch. Khim. 32 (1962) 403-407
40. J. Gen. Chem. USSR 32 (1962) 395-398
41. For difluoroketene acetals, see:. He Y., Junk C.P., Cawley J.J., and Lemal D.M. J. Am. Chem. Soc. 125 (2003) 5590-5591
42. Xu Y., Dolbier Jr. W.R., and Rong X.X. J. Org. Chem. 62 (1997) 1576-1577
43. Ding Y., Wang J., Abboud K.A., Xu Y., and Dolbier Jr. W.R. J. Org. Chem. 66 (2001) 6381-6388
44. For C-F bond cleavage reactions through β-elimination of fluoride, see:
45. Amii H., and Uneyama K. Chem. Rev. 109 (2009) 2119-2183
46. Uneyama K., Maeda K., Kato T., and Katagiri T. Tetrahedron Lett. 39 (1998) 3741-3744
47. Amii H., Kobayashi T., Hatamoto Y., and Uneyama K. Chem. Commun. (1999) 1323-1324
48. Jin F., Xu Y., and Huang W. J. Chem. Soc., Chem. Commun. (1993) 814-816
49. Brigaud T., Doussot P., and Portella C. J. Chem. Soc., Chem. Commun. (1994) 2117-2118
50. For the formation of difluoroketene N,O-acetal from trifluoroacetaldehyde N,O-acetal and its nucleophilicity, see:. Blond G., Billard T., and Langlois B.R. Chem.-Eur. J. 8 (2002) 2917-2922
51. Review on synthetic utility of N,O-acetal functionality, see:. Yamazaki N., and Kibayashi C. Product class 1: O,N-acetals. In: Otera J. (Ed). Science of Synthesis, Houben-Weyl Methods of Molecular Transformations Vol. 30 (2007), Georg Thieme, Stuttgart 7-19
52. Yanai H., and Taguchi T. Chem. Commun. (2009) 1034-1036
53. Yanai H., Ichikawa T., and Taguchi T. Tetrahedron Lett. 51 (2010) 2625-2628
54. Difluoromethylketone N,O-acetals were generally unstable on neutral silica gel, while chromatographic purification by short silica gel pad resulted in the reasonable isolated yield of these products.
55. 2O quench of the reaction mixture of 1a and n-BuLi, deuterium introduction at difluoromethinic position of 2aa was observed.
56. It was reported that Zn reduction of trichloroacetaldehyde results in the polymerization, see:. Shchepin V.V., Russkikh N.Y., Lapkin I.I., and Kyuntsel I.A. Zh. Org. Khim. 23 (1987) 503-505
57. J. Org. Chem. USSR 23 (1987) 453-455
58. For the Reformatsky reaction of trichloroacetates, see:
59. Miller R.E., and Nord F.F. J. Org. Chem. 16 (1951) 728-740
60. Castro B., Villieras J., and Ferracutti N. Bull. Soc. Chim. Fr. (1969) 3521-3522
61. Defluorination reaction of 2,2,2-trifluoroethyl ethers by alkyllithium reagents is well known:
62. Percy J.M. Tetrahedron Lett. 31 (1990) 3931-3932
63. Patel S.T., Percy J.M., and Wilkes R.D. Tetrahedron 51 (1995) 9201-9216
64. Howarth J.A., Owton W.M., Percy J.M., and Rock M.H. Tetrahedron 51 (1995) 10289-10302
65. Tanaka K., Shiraishi S., Nakai T., and Ishikawa N. Tetrahedron Lett. (1978) 3103-3106
66. Kocienski P.J., and Snaddon T.N. Org. Synth. 85 (2008) 45-52
67. 3 with n-BuLi.
68. Tanaka K., Nakai T., and Ishikawa N. Tetrahedron Lett. (1978) 4809-4810
69. Ichikawa J., Hamada S., Sonoda T., and Kobayashi H. Tetrahedron Lett. 33 (1992) 337-340
70. Yang S.-C., Lai H.-C., and Tsai Y.-C. Tetrahedron Lett. 45 (2004) 2693-2697
71. Masuoka Y., Asako T., Goto G., and Noguchi S. Chem. Pharm. Bull. 34 (1986) 130-139