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Synthesis 2003(14): 2189-2193
DOI: 10.1055/s-2003-41017
DOI: 10.1055/s-2003-41017
PAPER
© Georg Thieme Verlag Stuttgart · New York
Efficient Addition of Allylsilanes to α,β-Enones Using Catalytic Indium and Trimethylsilyl Chloride
Weitere Informationen
Received
3 June 2003
Publikationsdatum:
19. August 2003 (online)
Publikationsverlauf
Publikationsdatum:
19. August 2003 (online)
Abstract
α,β-Enones undergo an efficient Hosomi-Sakurai reaction with allyltrimethylsilane, in which a catalytic amount of indium is used in the presence of trimethylsilyl chloride as an activator under mild conditions to produce the conjugate addition products in good yields.
Key words
addition reactions - catalysis - indium - Michael additions - silicon
-
1a
Hosomi A.Sakurai H. J. Am. Chem. Soc. 1977, 99: 1673 -
1b
Ojima I.Kumagai M.Miyazawa Y. Tetrahedron Lett. 1977, 18: 1385 -
1c
Pardo R.Zahra J.-P.Santelli M. Tetrahedron Lett. 1979, 20: 4557 -
1d
Fleming I.Paterson I. Synthesis 1979, 446 -
1e
Yanami T.Miyashita M.Yoshikoshi A. J. Org. Chem. 1980, 45: 607 -
1f
Hosomi K.Kobayashi H.Sakurai H. Tetrahedron Lett. 1980, 21: 955 -
1g
Colvin E. Silicon in Organic Synthesis Butterworths; London: 1981. p.97 -
1h
Weber WP. Silicon Reagents for Organic Synthesis Vol. 12: Springer; Berlin: 1983. p.173 -
1i
Majetich G.Casares AM.Chapman D.Behnke M. Tetrahedron Lett. 1983, 24: 1909 -
1j
Blumenkopf TA.Heathcock CH. J. Am. Chem. Soc. 1983, 105: 2354 -
1k
Hosomi A. Acc. Chem. Res. 1988, 21: 200 -
1l
Fleming I.Dunogues J.Smithers R. Org. React. 1989, 37: 57 -
1m
Langkopf E.Schinzer D. Chem. Rev. 1995, 95: 1375 -
1n
Yadav JS.Reddy BVS.Sadasiv K.Satheesh G. Tetrahedron Lett. 2002, 43: 9695 -
2a
Dauben WG.Friedrich LF.Oberhansli P.Aoyagi EI. J. Org. Chem. 1972, 37: 9 -
2b
Heathcock CH.Kleinman EF.Binkley ES. J. Am. Chem. Soc. 1982, 104: 1054 -
2c
Majetich G.Behnke M.Hull K. J. Org. Chem. 1985, 50: 3615 -
2d
Tokoroyama T.Tsukamoto M.Asada T.Iio H. Tetrahedron Lett. 1987, 28: 6645 -
2e
Majetich G.Hull K. Tetrahedron 1987, 43: 5621 -
2f
Majetich G.Ringold C. Heterocycles 1987, 25: 271 -
2g
Majetich G.Defauw J. Tetahedron 1988, 44: 3833 -
2h
Yamamoto Y.Furuta T. J. Org. Chem. 1990, 55: 3971 -
2i
Majetich G.Song J.-S.Ringold C.Nemeth GA. Tetrahedron Lett. 1990, 31: 2239 -
2j
Majetich G.Lowery D.Khetani V.Song J.-S.Hull K.Ringold C. J. Org. Chem. 1991, 56: 3988 -
2k
Nakamura H.Oya T.Murai A. Bull. Chem. Soc. Jpn. 1992, 65: 929 -
2l
Schinzer D.Feber K.Puppelt M. Justus Liebigs Ann. Chem. 1992, 139 -
2m
Majetich G.Song J.-S.Leigh AJ.Condon SM. J. Org. Chem. 1993, 58: 1030 -
2n
Kuroda C.Inoue S.Takemura R.Satoh JY. J. Chem. Soc., Perkin Trans. 1 1994, 521 -
3a
Lee PH.Lee K.Sung S.-Y.Chang S. J. Org. Chem. 2001, 66: 8646 -
3b
Onishi Y.Ito T.Yasuda M.Baba A. Tetrahedron 2002, 58: 8227 -
3c
Onishi Y.Ito T.Yasuda M.Baba A. Eur. J. Org. Chem. 2002, 1578 - 4
Yanagisawa A.Habaue S.Yasue K.Yamamoto H. J. Am. Chem. Soc. 1994, 116: 6130 -
5a
Lipshutz BH.Ellsworth EL.Dimock SH.Smith RAJ. J. Am. Chem. Soc. 1990, 112: 4404 -
5b
Lipshutz BH.Hackmann C. J. Org. Chem. 1994, 59: 7437 -
6a
Lee PH.Ahn H.Lee K.Sung S.-Y.Kim S. Tetrahedron Lett. 2001, 42: 37 -
6b
Lee PH.Lee K.Kim S. Org. Lett. 2001, 3: 3205 -
6c
Iwasawa N.Miura T.Kiyota K.Kusama H.Lee K.Lee PH. Org. Lett. 2002, 4: 4463 - 7
Miura T.Kiyota K.Kusama H.Lee K.Kim H.Kim S.Lee PH.Iwasawa N. Org. Lett. 2003, 5: 1725 - 8
Shibata I.Kano T.Kanazawa N.Fukuoka S.Baba A. Angew. Chem. Int. Ed. 2002, 41: 1389 -
9a
Lee PH.Bang K.Lee K.Lee C.-H.Chang S. Tetrahedron Lett. 2000, 41: 7521 -
9b
Lee PH.Sung S.-Y.Lee K. Org. Lett. 2001, 3: 3201 -
9c
Lee PH.Lee K.Chang S. Synth. Commun. 2001, 31: 3189 -
9d
Lee PH.Bang K.Lee K.Sung S.-Y.Chang S. Synth. Commun. 2001, 31: 3781 -
9e
Lee PH.Bang K.Ahn H.Lee K. Bull. Korean Chem. Soc. 2001, 22: 1385 -
9f
Lee PH.Seomoon S.Lee K. Bull. Korean Chem. Soc. 2001, 22: 1380 -
9g
Bang K.Lee K.Park YK.Lee PH. Bull. Korean Chem. Soc. 2002, 23: 1272 -
9h
Lee PH.Sung S.-Y.Lee K.Chang S. Synlett 2002, 146 -
9i
Lee K.Seomoon D.Lee PH. Angew. Chem. Int. Ed. 2002, 41: 3901 -
9j
Lee K.Lee J.Lee PH. J. Org. Chem. 2002, 67: 8265 -
9k
Lee PH.Seomoon D.Lee K.Heo Y. J. Org. Chem. 2003, 68: 2510 -
9l
Lee PH.Lee SW.Lee K. Org. Lett. 2003, 5: 1103 -
11a
Wilson SR.Price MF. J. Am. Chem. Soc. 1982, 104: 1124 -
11b
Majetich G.Desmond R.Casares AM. Tetrahedron Lett. 1983, 24: 1913 -
11c
Tokoroyama T.Tsukamoto M.Iio H. Tetrahedron Lett. 1984, 25: 5067 -
11d
Schinzer D. Angew. Chem., Int. Ed. Engl. 1984, 23: 308 -
11e
Schinzer D.Solyom S.Becker M. Tetrahedron Lett. 1985, 26: 1831 -
11f
Majetich G.Defauw J.Hull K.Shawe T. Tetrahedron Lett. 1985, 26: 4711 -
11g
Majetich G.Hull K.Defauw J.Shawe T. Tetrahedron Lett. 1985, 26: 2755 -
11h
Schinzer D. Synthesis 1988, 263 -
11i
Schinzer D.Allagiannis C.Wichmann S. Tetrahedron 1988, 44: 3851 -
11j
Schinzer D.Ringe K. Synlett 1994, 463 -
11k
Kuhnert N.Peverley J.Robertson J. Tetrahedron Lett. 1998, 39: 3215 - 13
Stork G.Reynolds ME. J. Am. Chem. Soc. 1988, 110: 6911 - Support for the formation of such TMSCl-α,β-enone complexes is lacking; 1H NMR measurement for a mixture of 2-cyclohexen-1-one and TMSCl failed to detect the Lewis acid-Lewis base complex:
-
14a
Corey EJ.Boaz NW. Tetrahedron Lett. 1985, 26: 6015 -
14b
Corey EJ.Boaz NW. Tetrahedron Lett. 1985, 26: 6019
References
14a was prepared from 1,3-cyclohexadione in 5 steps (PhH, EtOH, TsOH; LDA, allyl iodide; DIBALH; H3O+; Wacker oxidation).
12Compound 15a was prepared from 1,3-cyclohexadione in 7 steps (PhH, EtOH, TsOH; LDA, allyl iodide; Sia2BH, H2O2, NaOH; Swern oxidation; Ph3P=CHCH2TMS; DIBALH; H3O+).