A synthesis of di- and tri-substituted β,γ-unsaturated esters from aldehydes by the magnesium carbenoid 1,2-CH and 1,2-CC insertion as the key reaction

Tetrahedron

Volumn 65, Issue 3, 2009, Pages 613-627

  Yamashita, Hironori ^a   Satoh, Tsuyoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

, Unsaturated ester; 1,2 CC insertion; 1,2 CH insertion; Magnesium carbenoid; Sulfoxide magnesium exchange reaction

Indexed keywords

1 CHLORO 2 (2 FURYL) 1 (4 TOLYLSULFINYL)ETHENE; 1 CHLORO 2 (2 THIENYL) 1 (4 TOLYLSULFINYL)ETHENE; 1 CHLORO 2 (4 DIMETHYLAMINOPHENYL) 1 (4 TOLYLSULFINYL)ETHENE; 1 CHLORO 2 (4 METHOXYPHENYL) 1 (4 TOLYLSULFINYL)ETHENE; 1 CHLORO 2 (4 METHYLTHIOPHENYL) 1 (4 TOLYLSULFINYL)ETHENE; 1 CHLORO 2 PIPERONYL 1 (4 TOLYLSULFINYL)ETHENE; ALDEHYDE; CARBENOID; CARBON; ESTER; GRIGNARD REAGENT; LITHIUM DERIVATIVE; TERT BUTYL 3 (1 NAPHETHYL) 3 BUTENOATE; TERT BUTYL 3 (4 CYANOPHENYL) 3 BUTENOATE; TERT BUTYL 3 (4 METHOXYPHENYL) 3 BUTENOATE; TERT BUTYL 3 CYCLOHEXYL 3 BUTENOATE; TERT BUTYL 3 METHYLIDENE 5 PHNEYLPENTANOATE; TERT BUTYL 3 METHYLIDENENONANOATE; TERT BUTYL 3 PHENYL 3 BUTENOATE; TERT BUTYL 4 (4 METHOXYPHENYL) 3 BUTENOATE; TERT BUTYL 4 CHLORO 3 (1 NAPHTHYL) 4 (4 TOTYLSULFINYL)BUTYRATE; TERT BUTYL 4 CHLORO 3 (1,1 DIMETHYLETHYL) 4 (4 TOTYLSULFINYL)BUTYRATE; TERT BUTYL 4 CHLORO 3 (4 CYANOPHENYL) 4 (4 TOTYLSULFINYL)BUTYRATE; TERT BUTYL 4 CHLORO 3 (4 DIMETHYLAMINOPHENYL) 4 (4 TOLYLSULFINYL)BUTANOATE; TERT BUTYL 4 CHLORO 3 (4 METHOXYPHENYL) 4 (4 TOLYLSULFINYL)BUTANOATE; TERT BUTYL 4 CHLORO 3 CYCLOHEXYL 4 (4 TOTYLSULFINYL)BUTYRATE; TERT BUTYL 4 CHLORO 3 HEXYL 4 (4 TOTYLSULFINYL)BUTYRATE; TERT BUTYL 4 CHLORO 3 PHENYL 4 (4 TOTYLSULFINYL)BUTYRATE; TERT BUTYL 4,4 DIMETHYL 3 METHYLIDENEPENTANOATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CONFORMATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 57149143431     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.013     Document Type: Article

References (49)

1. Some monographs for the chemistry of carboxylic acids and their derivatives:
2. Patai S. The Chemistry of Carboxylic Acids and Esters (1969), John Wiley and Sons, London
3. Zabicky J. The Chemistry of Amides (1970), John Wiley and Sons, London
4. Patai S. The Chemistry of Acid Derivatives (1979), John Wiley and Sons, Chichester Parts 1 and 2
5. In: Sutherland I.O. (Ed). Comprehensive Organic Chemistry Vol. 2 (1979), Pergamon, Oxford Part 9
6. Patai S. The Chemistry of Acid Derivatives (1992), John Wiley and Sons, Chichester Parts 1 and 2
7. For example:
8. In: Barrett G.C. (Ed). Chemistry and Biochemistry of the Amino Acids (1985), Chapmann and Hall, London
9. Williams R.M. Synthesis of Optically Active α-Amino Acids (1989), Pergamon, Oxford
10. In: Juaristi E. (Ed). Enantioselective Synthesis of β-Amino Acids (1997), Wiley-VCH, New York, NY
11. For example:
12. Trost B.M., Salzmann T.N., and Hiroi K. J. Am. Chem. Soc. 98 (1976) 4887
13. Clive D.L. Tetrahedron 34 (1978) 1049
14. Wadsworth Jr. W.S. Org. React. 25 (1977) 73
15. Maryanoff B.E., and Reitz A.B. Chem. Rev. 89 (1989) 863
16. Shen Y. Acc. Chem. Res. 31 (1998) 584
17. Ando K. J. Synth. Org. Chem. Jpn. 58 (2000) 869
18. Hassner A., and Stumer C. Organic Synthesis Based on Name Reactions (2002), Pergamon, Amsterdam
19. Mundy B.P., Ellerd M.G., and Favaloro Jr. F.G. Name reactions and Reagents in Organic Synthesis. 2nd ed. (2005), Wiley-Interscience, Hoboken, NJ
20. Li J.J. Name Reactions. 3rd ed. (2006), Springer, Berlin
21. Kowalski C.J., Haque M.S., and Fields K. J. Am. Chem. Soc. 107 (1985) 1429
22. Kowalski C.J., and Reddy R. J. Org. Chem. 57 (1992) 7194
23. Satoh T., Nakamura A., Iriuchijima A., Hayashi Y., and Kubota K. Tetrahedron 57 (2001) 9689
24. Krebs E.-P. Helv. Chim. Acta 64 (1981) 1023
25. Ikeda Y., Ukai J., Ikeda N., and Yamamoto H. Tetrahedron 43 (1987) 743
26. Piva O. Tetrahedron 50 (1994) 13687
27. Kende A.S., and Todeer B.H. J. Org. Chem. 47 (1982) 167
28. Murphy K.E., and Hoveyda A.H. J. Am. Chem. Soc. 125 (2003) 4690
29. Hirao T., Fujihara Y., Kurokawa K., Ohsiro Y., and Agawa T. J. Org. Chem. 51 (1986) 2830
30. Ragoussis N. Tetrahedron Lett. 28 (1987) 93
31. Deng M.-Z., Li N.-S., and Huang Y.-Z. J. Org. Chem. 57 (1992) 4017
32. Deng M.-Z., Li N.-S., and Huang Y.-Z. J. Org. Chem. 58 (1993) 1949
33. Ballini R., Bosica G., and Fiorini D. Tetrahedron Lett. 42 (2001) 8471
34. Shen Y., and Ni J. J. Fluorine Chem. 124 (2003) 65
35. Satoh T. Chem. Soc. Rev. 36 (2007) 1561
36. Satoh T. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organomagnesium Compounds (2008), John Wiley and Sons, Chichester 717-769
37. Satoh T., Musashi J., and Kondo A. Tetrahedron Lett. 46 (2005) 599
38. Satoh T., Hayashi Y., and Yamakawa K. Bull. Chem. Soc. Jpn. 66 (1993) 1866
39. Sugiyama S., and Satoh T. Tetrahedron: Asymmetry 16 (2005) 665
40. Preliminary results of this investigation were reported as a Letter:. Satoh T., Yamashita H., and Musashi J. Tetrahedron Lett. 48 (2007) 7295
41. Ogata S., Masaoka S., Sakai K., and Satoh T. Tetrahedron Lett. 48 (2007) 5017
42. Ogata S., Saitoh H., Wakasugi D., and Satoh T. Tetrahedron 64 (2008) 5711
43. Westwell A.D., and Rayner C.M. In: Page P. (Ed). Organosulfur Chemistry Vol. 2 (1998), Academic, San Diego 157-228
44. Satoh T., and Sugiyama S. J. Synth. Org. Chem. Jpn. 64 (2006) 1049
45. Satoh T., Kobayashi S., Nakanishi S., Horiguchi K., and Irisa S. Tetrahedron 55 (1999) 2515
46. Hoffmann R.W., Holzer B., Knopff O., and Harms K. Angew. Chem., Int. Ed. 39 (2000) 3072
47. Satoh T., Matsue R., Fujii T., and Morikawa S. Tetrahedron 57 (2001) 3891
48. Hoffmann R.W. Chem. Soc. Rev. 32 (2003) 225
49. Satoh T., and Ota H. Tetrahedron 56 (2000) 5113