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Synthesis 2002(16): 2319-2334
DOI: 10.1055/s-2002-35231
DOI: 10.1055/s-2002-35231
REVIEW
© Georg Thieme Verlag Stuttgart · New York
The 2-(Trimethylsilyl)ethyl Sulfur Group in Synthesis
Further Information
Received
11 September 2002
Publication Date:
04 November 2002 (online)
Publication History
Publication Date:
04 November 2002 (online)
Abstract
The trimethylsilylethyl sulfur group present in 2-(trimethylsilyl)ethyl sulfides, sulfones, sulfoxides and in 2-(trimethylsilyl)ethylsulfonamido derivatives has proved its potential in synthesis. Presence of sulfur and silicon on adjacent carbon atoms provides routes for preparing interesting sulfur or non-sulfur, silicon or non-silicon derivatives like thiols, methyl disulfides, thioesters, thiocyanates, unsaturated derivatives and amines through the selective removal of the trimethylsilylethyl or the trimethylsilyl group.
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1 Introduction
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2 Synthesis and Reactions of 2-(Trimethylsilyl)ethyl Sulfides
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2.1 Synthesis of 2-(Trimethylsilyl)ethanethiol and Derivatives
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2.2 Reactions of 2-(Trimethylsilyl)ethyl Sulfides
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2.2.1 Synthesis of Non-silylated Thiols and Disulfides
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2.2.2 Other Reactions of 2-(Trimethylsilyl)ethyl Sulfides
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2.2.2.1 Synthesis of 2-(Trimethylsilyl)ethyl Sulfinimides
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2.2.2.2 Removal of the 2-(Trimethylsilyl)ethyl Group and Synthesis of Sulfur Derivatives
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3 2-(Trimethylsilyl)ethyl Sulfones and Sulfoxides
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3.1 Sulfones
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3.2 Sulfoxides
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4 2-(Trimethylsilyl)ethylsulfonamido Derivatives
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4.1 The 2-(Trimethylsilyl)ethylsulfonamido Protecting Group
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4.2 2-(Trimethylsilyl)ethylsulfonamide (SES-NH2)
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4.3 The SES-NH-Boc Derivative
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4.4 N-Sulfinyl-[2-(trimethylsilyl)ethyl]sulfonamide
(SES-NSO) -
4.5 Di[2-(trimethylsilyl)ethyl]sulfodiimide
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4.6 Other Reagents for the Synthesis of SES-protected Amines
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5 Conclusion
Key words
2-(trimethylsilyl)ethyl - sulfur - sufones - sulfoxides - vinyl anion - alkenes - dienes - alkynes - 2-(trimethylsilyl)ethylsulfonamido
- 1
Block E.Aslam M. Tetrahedron 1988, 44: 281 - 2
Apeloig Y.Stanger A. J. Am. Chem. Soc. 1985, 107: 2806 - 3
Wierschke SG.Chandrasekhar J.Jorgensen WL. J. Am. Chem. Soc. 1985, 107: 1496 - 4
Lambert JB.Wang G.-T.Finzel RB.Teramura DH. J. Am. Chem. Soc. 1987, 109 : 7838 - 5
Chambert S.Décout J.-L. Org. Prep. Proced. Int. 2002, 34: 27 - 6
Baird CP.Rayner CM. J. Chem. Soc., Perkin Trans. 1 1998, 1973 - 7
Procter DJ. J. Chem. Soc., Perkin Trans. 1 1999, 641 - 8
Procter DJ. J. Chem. Soc., Perkin Trans. 1 2000, 835 - 9
Procter DJ. J. Chem. Soc., Perkin Trans. 1 2001, 335 - 10
Schwan AL.Dufault R. Tetrahedron Lett. 1992, 33: 3973 - 11
Mahadevan A.Li C.Fuch PL. Synth. Commun. 1994, 24: 3099 - 12
Yu CJ.Chong Y.Kayyem JF.Gozin M. J. Org. Chem. 1999, 64: 2070 - 13
Schwan AL.Brillon D.Dufault R. Can. J. Chem. 1994, 72: 325 - 14
Schwan AL.Strickler RR.Dunn-Dufault R.Brillon D. Eur. J. Org. Chem. 2001, 1643 - 15
Griesbaum K. Angew. Chem., Int. Ed. Engl. 1970, 9: 273 - 16
Wetterlin K. Acta Chem. Scand. 1964, 18: 899 - 17
Gornowicz GA.Ryan JW.Speier JL. J. Org. Chem. 1968, 33: 2918 - 18
Ito TI.Weber WP. J. Org. Chem. 1974, 39: 1694 - 19
Anderson MB.Ranasinghe MG.Palmer JT.Fuchs PL. J. Org. Chem. 1988, 53: 3125 - 20
Stamm W. J. Org. Chem. 1963, 28: 3264 - 21
Brill WK.-D.Tirefort D. Tetrahedron Lett. 1998, 39: 787 - 22
Chambert S.Thomasson F.Décout J.-L. J. Org. Chem. 2002, 67: 1898 - 23
Ranasinghe MG.Fuchs PL. Synth. Commun. 1988, 18: 227 - 24
Ranasinghe MG.Fuchs PL. J. Am. Chem. Soc. 1989, 111: 779 - 25
Takeda H.Shimada S.Ohnishi S.Nakanishi F.Matsuda H. Tetrahedron Lett. 1998, 39: 3701 - 26
Baum G.Kaiser F.-J.Massa W.Seitz G. Angew. Chem., Int. Ed. Engl. 1987, 26: 1163 - 27
Koreeda MY.Yang W. J. Am. Chem. Soc. 1994, 116: 10793 - 28
Wang Y.Koreeda M. J. Org. Chem. 1998, 63: 8644 - 29
Covès J.Le Hir de Fallois L.Le Pape L.Décout J.-L.Fontecave M. Biochemistry 1996, 35: 8595 - 30
Le Hir de Fallois L.Décout J.-L.Fontecave M. J. Chem. Soc, Perkin Trans. 1 1997, 2587 - 31
Chambert S.Gautier-Luneau I.Fontecave M.Décout J.-L. J. Org. Chem. 2000, 65: 249 - 32
Suslova EN.Kirpichenko SV.Albanov AI.Shainyan BA. J. Chem. Soc., Perkin Trans. 1 2000, 3140 - 33
Nilsson U.Ray AK.Magnusson G. Carbohydr. Res. 1994, 252: 117 - 34
Grundberg H.Andergran M.Nilsson UJ. Tetrahedron Lett. 1999, 40: 1811 - 35
Fuchs PL.Braish TF. Chem. Rev. 1986, 86: 903 - 36
Prilezhaeva EN. Russ. Chem. Rev. 2000, 69: 367 - 37
Braverman S.Cherkinsky M.Raj P. Sulfur Reports 1999, 22: 49 - 38
Carretero JC.Arrayas RG.Buezo ND.Garrido JL.Alonso I.Adrio J. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 153 - 39
Prilezhaeva EN. Russ. Chem. Rev. 2001, 70: 897 - 40
Hsiao C.-N.Shechter H. J. Org. Chem. 1988, 53: 2688 - 41
Palmer JT.Fuchs PL. Synth. Commun. 1988, 18: 233 - 42
Henriques RG.Widlanski TS.Xu T.Lambeth JD. J. Am. Chem. Soc. 1992, 114: 7311 - 43
Kocienski PJ. Tetrahedron Lett. 1979, 28: 2649 - 44
Kocienski PJ. J. Org. Chem. 1980, 45: 2037 - 45
Hsiao C.-N.Shechter H. Tetrahedron Lett. 1982, 23: 3455 - 46
Kim SH.Jin Z.Ma S.Fuchs PL. Tetrahedron Lett. 1995, 36: 4013 - 47
Carr RVC.Williams RV.Paquette LA. J. Org. Chem. 1983, 48: 4976 - 48
Williams RV.Chauhan K.Gadgil VR. J. Chem. Soc., Chem. Commun. 1994, 1739 - 49
Hsiao C.-N.Shechter H. Organomet. Chem. 1985, 285: 121 - 50
Meagher TP.Yet L.Hsiao C.-N.Shechter H. J. Org. Chem. 1998, 63: 4181 - 51
Kabat MM.Wicha J. Tetrahedron Lett. 1991, 32: 1073 - 52
Hsiao C.-N.Shechter H. Tetrahedron Lett. 1984, 25: 1219 - 53
Lenihan BD.Shechter H. J. Org. Chem. 1998, 63: 2072 - 54
Lenihan BD.Shechter H. J. Org. Chem. 1998, 63: 2086 - 55
Menichetti S.Griffiths G.Stirling CJM. J. Chem. Soc., Chem. Commun. 1992, 54 - 56
Menichetti S.Stirling CJM. J. Chem. Soc., Perkin Trans. 2 1992, 741 - 57
Menichetti S.Stirling CJM. J. Chem. Soc., Perkin Trans. 1 1996, 1511 - 58
Menichetti S.Stirling CJM. J. Chem. Soc., Perkin Trans. 1 2002, 1: 28 - 59
Matsuyama H. Sulfur Reports 1999, 22: 85 - 60
Allin SM.Shuttleworth SJ.Bulman Page PC. Organosulfur Chemistry 1998, 2: 97 - 61
Fleming I.Goldhill J.Perry DA. J. Chem. Soc., Perkin Trans. 1 1982, 1563 - 62
Ochiai M.Tada S.-I.Sumi K.Fujita E. J. Chem. Soc., Chem. Commun. 1982, 281 - 63
Hsiao C.-N.Shechter H. Tetrahedron Lett. 1983, 24: 2371 - 64
Schwan AL.Pippert MF. Tetrahedron: Asymmetry 1995, 6: 131 - 65
Davis FA.Reddy RT.Han W.Carroll PJ. J. Am. Chem. Soc. 1992, 114: 1428 - 66
Solladié G.Hutt J.Girardin A. Synthesis 1987, 173 - 67
Kusuda S.Ueno Y.Toru T. Tetrahedron 1994, 50: 1045 - 68
Nakamura S.Takemoto H.Ueno Y.Toru T.Kakumoto T.Hagiwara T. J. Org. Chem. 2000, 65: 469 - 69
Nakamura S.Uchiyama Y.Ishikawa S.Fukinbara R.Watanabe Y.Toru T. Tetrahedron Lett. 2002, 43: 2381 - 70
Nakamura S.Watanabe Y.Toru T. J. Chem. Soc., Perkin Trans. 1 1999, 3403 - 71
Nakamura S.Watanabe Y.Toru T. J. Org. Chem. 2000, 65: 1758 - 72
Kusuda S.Kawamura K.Ueno Y.Toru T. Tetrahedron Lett. 1993, 34: 6587 - 73
Nakamura S.Kusuda S.Kamamura K.Toru T. J. Org. Chem. 2002, 67: 640 - 74
Toru T.Nakamura S.Takemoto H.Ueno Y. Synlett 1997, 449 - 75
Schwan AL.Kalin ML.Vajda KE.Xiang T.-J.Brillon D. Tetrahedron Lett. 1996, 37: 2345 - 76
Weinreb SM.Demko DM.Lessen TA.Demers JP. Tetrahedron Lett. 1986, 27: 2099 - 77
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis John Wiley and Sons; New York: 1999. - 78
KocieŇski PJ. Protecting Groups Thieme; Stuttgart: 1994. - 79
Weinreb SM.Ralbovsky JL. Handbook of Reagents for Organic Synthesis - Activating Reagents and Protecting Groups John Wiley and Sons; New York: 1999. - 80
Huang J.Widlanski TS. Tetrahedron Lett. 1992, 33: 2657 - 81
Matzanke N.Gregg RJ.Weinreb SM. J. Org. Chem. 1997, 62: 1920 - 82
Ward DE.Gai Y.Kaller BF. J. Org. Chem. 1996, 61: 5498 - 83
Xu Z.Lu X. J. Org. Chem. 1998, 63: 5031 - 84
Kozlowski MC.Bartlett PA. J. Org. Chem. 1996, 61: 7681 - 85
Boger DL.Ledeboer MW.Kume M.Searcey M.Jin Q. J. Am. Chem. Soc. 1999, 121: 11375 - 86
Pak JK.Guggisberg A.Hesse M. Tetrahedron 1998, 54: 8035 - 87
Pak JK.Hesse M. Helv. Chim. Acta 1998, 81: 2301 - 88
Pak JK.Hesse M. J. Org. Chem. 1998, 63: 8200 - 89
Wipf P.Venkatraman S. J. Org. Chem. 1995, 60: 7224 - 90
Wipf P.Venkatraman S.Miller CP. Tetrahedron Lett. 1995, 36 - 91
Ferraris D.Dudding T.Young B.Drury WJ.Lectka T. J. Org. Chem. 1999, 64: 2168 - 92
Ferraris D.Young B.Dudding T.Drury WJ.Lectka T. Tetrahedron 1999, 55: 8869 - 93
Boger DL.Chen J.-H.Saionz KW. J. Am. Chem. Soc. 1996, 118: 1629 - 94
Boger DL.Schüle G. J. Org. Chem. 1998, 63: 6421 - 95
Nouvet A.Binard M.Mamaty F.Martinez J.Lazaro R. Tetrahedron 1999, 55: 4685 - 96
Danishefsky SJ.Koseki K.Griffith DA.Gervay J.Peterson JM.McDonald FE.Oriyama T. J. Am. Chem. Soc. 1992, 114: 8331 - 97
Danishefsky SJ.Gervay J.Peterson JM.McDonald FE.Koseki K.Griffith DA.Oriyama T.Mardsen SP. J. Am. Chem. Soc. 1995, 117: 1940 - 98
Ritzeler O.Hennig L.Findeisen M.Welzel P.Müller D. Tetrahedron 1997, 53: 1665 - 99
Zhang H.-Y.Yu J.-Q.Bruice T. Tetrahedron 1994, 50: 11339 - 100
Li S.Kosemura S.Yamamura S. Tetrahedron Lett. 1994, 35: 8217 - 101
Li S.Ohba S.Kosemura S.Yamamura S. Tetrahedron Lett. 1996, 37: 7365 - 102
Li S.Yamamura S. Tetrahedron Lett. 1998, 39: 2597 - 103
Li S.Yamamura S. Tetrahedron 1998, 54: 8691 - 104
Li S.Yamamura S.Hosomi H.Ohba S. Tetrahedron Lett. 1998, 39: 2601 - 105
Li S.Kosemura S.Yamamura S. Tetrahedron 1998, 54: 6661 - 106
Campbell JA.Hart DJ. Tetrahedron Lett. 1992, 33: 6247 - 107
Campbell JA.Hart DJ. J. Org. Chem. 1993, 58: 2900 - 108
Grillot A.-L.Hart DJ. Tetrahedron 1995, 51: 11377 - 109
Campbell JA.Rapoport H. J. Org. Chem. 1996, 61: 6313 - 110
Gao Y.Lane-Bell P.Vederas JC. J. Org. Chem. 1998, 63: 2133 - 111
Garigipati RS.Tschaen DM.Weinreb SM. J. Am. Chem. Soc. 1990, 112: 3475 - 112
Stien D.Anderson GT.Chase CE.Koh Y.-H.Weinreb SM. J. Am. Chem. Soc. 1999, 121: 9574 - 113
Kim YH.Shin JM. Tetrahedron Lett. 1985, 26: 3821 - 114
Sisko J.Weinreb SM. Tetrahedron Lett. 1989, 30: 3037 - 115
Sisko J.Weinreb SM. J. Org. Chem. 1990, 55: 393 - 116
Griffith DA.Danishefsky SJ. J. Am. Chem. Soc. 1996, 118: 9526 - 117
Aggarwal VK.Thompson A.Jones RVH.Standen MCH. J. Org. Chem. 1996, 61: 8368 - 118
Dauban P.Dodd RH. J. Org. Chem. 1999, 64: 5304