Synthesis of multi-substituted cyclobutanes and alkylidenecyclobutanes by the reaction of cyclobutylmagnesium carbenoids with nucleophiles

Synthesis

Volumn , Issue 3, 2011, Pages 397-408

  Satoh, Tsuyoshi ^a   Kasuya, Takashi ^a   Ishigaki, Masashi ^a   Inumaru, Mio ^a   Miyagawa, Toshifumi ^a   Nakaya, Nobuhito ^a   Sugiyama, Shimpei ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

alkylidenecyclobutane; cyclobutane; cyclobutylmagnesium carbenoid; cyclobutylmagnesium chloride; magnesium carbenoid

Indexed keywords

ALKYLIDENECYCLOBUTANE; CARBENOIDS; CYCLOBUTANES; CYCLOBUTYLMAGNESIUM CHLORIDE; GOOD YIELD; GRIGNARD REAGENT; HIGH YIELD; LOW TEMPERATURES; P-TOLYL;

BUTANE; LITHIUM; MAGNESIUM; NUCLEOPHILES; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

CHLORINE COMPOUNDS;

1 CHLOROCYCLOBUTYL 4 TOLYL SULFOXIDE; ALKYLIDENECYCLOBUTANE DERIVATIVE; CYCLOBUTANE DERIVATIVE; CYCLOPENTYLMAGNESIUM CHLORIDE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYLMAGNESIUM CARBENOID DERIVATIVE; ETHYLMAGNESIUM CHLORIDE; GRIGNARD REAGENT; ISOPROPYLMAGNESIUM CHLORIDE; LITHIUM ALPHA SULFONYL CARBANION; LITHIUM DERIVATIVE; NUCLEOPHILE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; LOW TEMPERATURE; SYNTHESIS; THERMOSTABILITY;

EID: 79151484349     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258391     Document Type: Article

References (51)

1. Some recent reviews on the chemistry, synthesis and synthetic uses of cyclobutanes:, Bellus D, Ernst B, Angew. Chem., Int. Ed. Engl. 1988 27 797
2. Bach T, Synthesis 1998 683
3. Lee-Ruff E, Mladenova G, Chem. Rev. 2003 103 1449
4. Namyslo J C., Kaufmann D E., Chem. Rev. 2003 103 1485
5. Sadana A K., Saini R K., Billups W E., Chem. Rev. 2003 103 1539
6. Papers concerning the chemistry of cyclopropylmagnesium carbenoids from our laboratories:, Satoh T, Kurihara T, Fujita K, Tetrahedron 2001 57 5369
7. Satoh T, Saito S, Tetrahedron Lett. 2004 45 347
8. Satoh T, Miura M, Sakai K, Yokoyama Y, Tetrahedron 2006 62 4253
9. Yamada Y, Miura M, Satoh T, Tetrahedron Lett. 2008 49 169
10. Miyagawa T, Tatenuma T, Tadokoro M, Satoh T, Tetrahedron 2008 64 5279
11. Satoh T, Nagamoto S, Yajima M, Yamada Y, Ohata Y, Tadokoro M, Tetrahedron Lett. 2008 49 5431
12. Satoh T, Noguchi T, Miyagawa T, Tetrahedron Lett. 2008 49 5689
13. Yajima M, Nonaka R, Yamashita H, Satoh T, Tetrahedron Lett. 2009 50 4754
14. Yamada Y, Mizuno M, Nagamoto S, Satoh T, Tetrahedron 2009 65 10025
15. Satoh T, Ikeda S, Miyagawa T, Noguchi T, Tetrahedron Lett. 2010 51 1955
16. Preliminary results of this study were reported as a Letter:, Satoh T, Kasuya T, Miyagawa T, Nakaya N, Synlett 2010 286
17. Satoh T, Chem. Soc. Rev. 2007 36 1561
18. Satoh T, In The Chemistry of Organomagnesium Compounds Rappoport Z Marek I Wiley Chichester 2008 717-769
19. Michejda C J., Comnick R W., J. Org. Chem. 1975 40 1046
20. Fyfe M C. T., Rasamison C M., Org. Prep. Proced. Int. 2005 37 194
21. Yoshida Y, Sakakura Y, Aso N, Okada S, Tanabe Y, Tetrahedron 1999 55 2183
22. Friedman L, Shechter H, J. Am. Chem. Soc. 1960 82 1002
23. Kammula S, Shevlin P B., J. Am. Chem. Soc. 1974 96 7830
24. Brinker U H., Weber J, Tetrahedron Lett. 1986 27 5371
25. Watanabe M, Nakamura M, Satoh T, Tetrahedron 2005 61 4409
26. Brandsma L, Verkruijsse H D., Synthesis of Acetylenes, Allenes and Cumulenes Elsevier Amsterdam 1981
27. Schuster H F., Coppola G M., Allenes in Organic Synthesis Wiley New York 1984
28. Oku M, Arai S, Katayama K, Shioiri T, Synlett 2000 493
29. Mori N, Obuchi K, Katae T, Sakurada J, Satoh T, Tetrahedron 2009 65 3509
30. Our recent reports concerning the reaction of magnesium carbenoids with nitrogen nucleophiles:, Satoh T, Osawa A, Kondo A, Tetrahedron Lett. 2004 45 6703
31. Satoh T, Miura M, Sakai K, Yokoyama Y, Tetrahedron 2006 62 4253
32. Sakurada J, Satoh T, Tetrahedron 2007 63 3806
33. Ohbayashi T, Mitsunaga S, Satoh T, Tetrahedron Lett. 2007 48 7829
34. Mitsunaga S, Ohbayashi T, Sugiyama S, Saitou T, Tadokoro M, Satoh T, Tetrahedron: Asymmetry 2009 20 1697
35. Yamada Y, Mizuno M, Nagamoto S, Satoh T, Tetrahedron 2009 65 10025
36. Some recent papers concerning the chemistry, synthesis, and synthetic uses of alkylidene cyclobutanes:, Narasaka K, Hayashi K, Hayashi Y, Tetrahedron 1994 50 4529
37. Zhang W, Dowd P, Tetrahedron Lett. 1995 36 8539
38. Shepard M S., Carreira E M., J. Am. Chem. Soc. 1997 119 2597
39. Hojo M, Murakami C, Nakamura S, Hosomi A, Chem. Lett. 1998 331
40. Fujiwara T, Iwasaki N, Takeda T, Chem. Lett. 1998 741
41. Baldwin J E., Shukla R, Org. Lett. 1999 1 1081
42. Gauvry N, Bhat L, Mevellec L, Zucco M, Huet F, Eur. J. Org. Chem. 2000 2717
43. Pizem H, Sharon O, Frimer A A., Tetrahedron 2002 58 3199
44. Chowdhury M A., Senboku H, Tokuda M, Tetrahedron Lett. 2003 44 3329
45. Jiang M, Liu L.-P, Shi M, Tetrahedron 2007 63 9599
46. Chen L, Shi M, Li C, Org. Lett. 2008 10 5285
47. Iwasaki M, Yorimitsu H, Oshima K, Synlett 2009 2177
48. Jiang M, Shi M, Tetrahedron 2009 65 798
49. Satoh T, Kondo A, Musashi J, Tetrahedron 2004 60 5453
50. Satoh T, Sakamoto T, Watanabe M, Tetrahedron Lett. 2002 43 2043
51. Satoh T, Sakamoto T, Watanabe M, Takano K, Chem. Pharm. Bull. 2003 51 966