Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2004(13): 2226-2235
DOI: 10.1055/s-2004-829186
DOI: 10.1055/s-2004-829186
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Stereocontrolled Formation of Vinylsilanes via Homolytic Substitution at Silicon
Further Information
Received
17 May 2004
Publication Date:
30 July 2004 (online)
Publication History
Publication Date:
30 July 2004 (online)
Abstract
Intramolecular homolytic substitution reactions at silicon by vinyl radicals are described. The reaction can be used for the formation of 5- and 6-membered cyclic alkoxysilanes bearing a vinyl silane functionality. These processes provide a new entry into highly substituted vinyl silanes. The reactions occur with moderate to excellent selectivities.
Key words
radical chemistry - silicon - stereoselective synthesis - vinyl silanes - tin
-
2a
Davis DD.Ahmed FU. J. Am. Chem. Soc. 1981, 103: 7653 -
2b
Ashcroft MR.Bury A.Cooksey CJ.Davies AG.Gupta BD.Johnson MD.Morris H. J. Organomet. Chem. 1980, 195: 89 -
2c
Gupta BD.Roy S. J. Chem. Soc., Perkin Trans. 2 1988, 1377 -
2d
Curran DP.Gabarda AE. Tetrahedron 1999, 55: 3327 -
2e
Shimakoshi H.Koga M.Hayashi T.Tachi Y.Naruta Y.Hisaeda Y. Chem. Lett. 2001, 346 - 3
Schiesser CH.Wild LM. Tetrahedron 1996, 52: 13265 - For recent work see:
-
4a
Matsubara H.Schiesser CH. J. Org. Chem. 2003, 68: 9299 ; and references cited therein -
4b
Horvat SM.Kim S.Schiesser CH. Chem. Commun. 2003, 1182 -
4c
Matsubara H.Horvat SM.Schiesser CH. Org. Biomol. Chem. 2003, 1: 1199 -
4d
Shuto S.Sugimoto I.Abe H.Matsuda A. J. Am. Chem. Soc. 2000, 122: 1343 -
4e
Kulicke KJ.Chatgilialoglu C.Kopping B.Giese B. Helv. Chim. Acta 1992, 75: 935 -
4f
Miura K.Oshima K.Utimoto K. Chem. Lett. 1992, 2477 - 5
Kim S.Do JY.Lim KM. Chem. Lett. 1996, 669 -
6a
Kim S.Lee S.Koh JS. J. Am. Chem. Soc. 1991, 113: 5106 -
6b
Kim S.Koh JS. J. Chem. Soc., Chem. Commun. 1992, 1377 -
6c
Ryu I.Kurihara A.Muraoka H.Tsunoi S.Kambe N.Sonoda N. J. Org. Chem. 1994, 59: 7570 -
6d
Hays DS.Fu GC. J. Org. Chem. 1998, 63: 6375 -
6e
Chang S.-Y.Shao Y.-F.Chu S.-F.Fan G.-T.Tsai Y.-M. Org. Lett. 1999, 1: 945 -
6f
Kim S.Jung MS.Cho CH.Schiesser CH. Tetrahedron Lett. 2001, 42: 943 -
7a
Studer A. Angew. Chem. Int. Ed. 1998, 37: 462 -
7b
Studer A.Steen H. Chem.-Eur. J. 1999, 5: 759 - These processes belong to Unimolecular Chain Transfer Reactions (UMCT):
-
8a
Curran DP.Xu J.Lazzarini E. J. Chem. Soc., Perkin Trans. 1 1995, 3049 -
8b
Curran DP.Xu J. J. Chem. Soc., Perkin Trans. 1 1995, 3061 -
8c
Curran DP.Xu J.Lazzarini E. J. Am. Chem. Soc. 1995, 117: 6603 -
8d
Martinez-Grau A.Curran DP. Tetrahedron 1997, 53: 5679 -
8e
Curran DP.Xu JY. Synlett 1997, 1102 -
9a
Studer A.Amrein S.Matsubara H.Schiesser CH.Doi T.Kawamura T.Fukuyama T.Ryu I. Chem. Commun. 2003, 1190 -
9b See also:
Matsubara H.Schiesser CH. Org. Biomol. Chem. 2003, 1: 4335 -
10a
Choi J.-K.Hart DJ.Tsai Y.-M. Tetrahedron Lett. 1982, 4765 -
10b
Stork G.Mook R. J. Am. Chem. Soc. 1983, 105: 3720 -
10c
Journet M.Magnol E.Smadja W.Malacria M. Synlett 1991, 58 -
10d
Lowinger TB.Weiler L. J. Org. Chem. 1992, 57: 6099 -
10e
Pradhan SK.Sitabkhan S. Tetrahedron Lett. 1993, 34: 5615 -
10f
Journet M.Malacria M. J. Org. Chem. 1992, 57: 3085 -
10g
Clive DLJ.Ardelean E.-S. J. Org. Chem. 2001, 66: 4841 ; and references cited therein - 11
Vedejs E.Arnost MJ.Hagen JP. J. Org. Chem. 1979, 44: 3230 -
12a
Frantz DE.Fässler R.Tomooka CS.Carreira EM. Acc. Chem. Res. 2000, 33: 373 -
12b
Pu L. Tetrahedron 2003, 59: 9873 - 13
Kawachi A.Doi N.Tamao K. J. Am. Chem. Soc. 1997, 119: 233 - 14
Curran DP.Chen M.-H.Kim D. J. Am. Chem. Soc. 1989, 111: 6265 - 15
Kamiya N.Chikami Y.Ishii Y. Synlett 1990, 675 - 16
Giese B. Angew. Chem. 1989, 101: 993 - 17
Ishiyama H.Ishibashi M.Ogawa A.Yoshida S.Kobayashi J. J. Org. Chem. 1997, 62: 3831 - 18
Marshall JA.Johns BA. J. Org. Chem. 1998, 63: 7885 -
19a
Denmark SE.Ober MH. Aldrichimica Acta 2003, 36: 75 -
19b
Denmark SE.Sweis RF. Acc. Chem. Res. 2002, 35: 835
References
New address: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany.