메뉴 건너뛰기




Volumn 73, Issue 14, 2008, Pages 5462-5475

Temporary silicon connection strategies in intramolecular allylation of aldehydes with allylsilanes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINES; CHEMICAL REACTIONS; ETHERS; NONMETALS; SILANES; SILICON;

EID: 48249088035     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800824x     Document Type: Article
Times cited : (18)

References (147)
  • 3
    • 0002446724 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon: Oxford, UK, Chapter 1.1, pp
    • (c) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 2, Chapter 1.1, pp 1-53.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1-53
    • Roush, W.R.1
  • 4
    • 0001579610 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon: Oxford, UK, Chapter 2.2, pp
    • (d) Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 2, Chapter 2.2, pp 563-593.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 563-593
    • Fleming, I.1
  • 11
    • 0000174207 scopus 로고
    • Additives, such as fluoride, which activate the allylsilane, have occasionally been used. In these cases, the nucleophile may be an allyl anion, see: a
    • Additives, such as fluoride, which activate the allylsilane, have occasionally been used. In these cases, the nucleophile may be an allyl anion, see: (a) Hosomi, A. Shirahata, A. Sakurai, H. Tetrahedron Lett. 1978, 3043-3046.
    • (1978) Tetrahedron Lett , pp. 3043-3046
    • Hosomi, A.1    Shirahata, A.2    Sakurai, H.3
  • 16
    • 33748428923 scopus 로고    scopus 로고
    • For computational investigations on the Lewis acid-mediated reaction of allyltrialkylsilanes with aldehydes see: (a) Tietze, L. F. Kinzel, T. Schmatz, S. J. Am. Chem. Soc. 2006, 128, 11483-11495
    • For computational investigations on the Lewis acid-mediated reaction of allyltrialkylsilanes with aldehydes see: (a) Tietze, L. F. Kinzel, T. Schmatz, S. J. Am. Chem. Soc. 2006, 128, 11483-11495.
  • 23
    • 0020173674 scopus 로고
    • For the classification of allyl metals see: a
    • For the classification of allyl metals see: (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 198221555-566.
    • (1982) Angew. Chem., Int. Ed. Engl , vol.21 , pp. 555-566
    • Hoffmann, R.W.1
  • 24
    • 48249115448 scopus 로고    scopus 로고
    • Reference 5c
    • (b) Reference 5c.
  • 33
    • 0026065102 scopus 로고    scopus 로고
    • Chiral allylsilanes, which incorporate stereochemical information into the β- and γ-sites, have also been investigated: (a) Nativi, C.; Palio, G.; Taddei, M. Tetrahedron Lett. 1991, 32, 1583-1586.
    • Chiral allylsilanes, which incorporate stereochemical information into the β- and γ-sites, have also been investigated: (a) Nativi, C.; Palio, G.; Taddei, M. Tetrahedron Lett. 1991, 32, 1583-1586.
  • 36
    • 33751499865 scopus 로고    scopus 로고
    • The use of allylsilanes containing chiral ligands had previously met with little success: (a) Nativi, C.; Ravida, N.; Ricci, A.; Seconi, G.; Taddei, M. J. Org. Chem. 1991, 56, 1951-1955.
    • The use of allylsilanes containing chiral ligands had previously met with little success: (a) Nativi, C.; Ravida, N.; Ricci, A.; Seconi, G.; Taddei, M. J. Org. Chem. 1991, 56, 1951-1955.
  • 40
    • 0001336337 scopus 로고    scopus 로고
    • Allylsilanes with Si-centered chirality have also been investigated: (a) Hathaway, S. J.; Paquette, L. A. J. Org. Chem. 1983, 48, 3351-3353.
    • Allylsilanes with Si-centered chirality have also been investigated: (a) Hathaway, S. J.; Paquette, L. A. J. Org. Chem. 1983, 48, 3351-3353.
  • 47
    • 33646555477 scopus 로고    scopus 로고
    • and references cited therein
    • (b) Orito, Y.; Nakajima, M. Synthesis 2006, 1391-1401, and references cited therein.
    • (2006) Synthesis , pp. 1391-1401
    • Orito, Y.1    Nakajima, M.2
  • 51
    • 0003157467 scopus 로고    scopus 로고
    • Diederich, F, Stang, P. J, Eds, Wiley-VCH: Weinheim, Germany, Chapter 10, pp
    • (a) Cox, L. R.; Ley, S. V. In Templated Organic Synthesis; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 10, pp 275-375.
    • (2000) Templated Organic Synthesis , pp. 275-375
    • Cox, L.R.1    Ley, S.V.2
  • 69
    • 85047699272 scopus 로고    scopus 로고
    • For related approaches used to probe this aspect of the allylation reaction see: a
    • For related approaches used to probe this aspect of the allylation reaction see: (a) Schlosser, M.; Franzini, L.; Bauer, C.; Leroux, F. Chem. Eur. J. 2001, 7, 1909-1914.
    • (2001) Chem. Eur. J , vol.7 , pp. 1909-1914
    • Schlosser, M.1    Franzini, L.2    Bauer, C.3    Leroux, F.4
  • 72
    • 0000032965 scopus 로고
    • For experimental studies employing related allyltrialkylstannanes see
    • For experimental studies employing related allyltrialkylstannanes see: Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133-5135.
    • (1994) J. Org. Chem , vol.59 , pp. 5133-5135
    • Denmark, S.E.1    Hosoi, S.2
  • 75
    • 48249142026 scopus 로고    scopus 로고
    • Part of this work was presented at the 2007 ACS meeting in Chicago.
    • Part of this work was presented at the 2007 ACS meeting in Chicago.
  • 77
    • 0027960686 scopus 로고    scopus 로고
    • TMS protection by using an aminosilane: (a) Tanabe, Y.; Murakami, M.; Kitaichi, K.; Yoshida, Y. Tetrahedron Lett. 1994, 35, 8409-8412.
    • TMS protection by using an aminosilane: (a) Tanabe, Y.; Murakami, M.; Kitaichi, K.; Yoshida, Y. Tetrahedron Lett. 1994, 35, 8409-8412.
  • 82
    • 0032492929 scopus 로고    scopus 로고
    • TES protection using an aminosilane: (a) Holton, R. A.; Zhang, Z.; Clarke, P. A.; Nadizadeh, H.; Procter, D. J. Tetrahedron Lett. 1998, 39, 2883-2886.
    • TES protection using an aminosilane: (a) Holton, R. A.; Zhang, Z.; Clarke, P. A.; Nadizadeh, H.; Procter, D. J. Tetrahedron Lett. 1998, 39, 2883-2886.
  • 83
    • 48249138342 scopus 로고    scopus 로고
    • TBDMS protection using an aminosilane: reference 31c.
    • TBDMS protection using an aminosilane: reference 31c.
  • 84
    • 0034346361 scopus 로고    scopus 로고
    • TIPS protection with an aminosilane: (a) Firouzabadi, H.; Iranpoor, N.; Shaterian, H. R. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 166, 71-82.
    • TIPS protection with an aminosilane: (a) Firouzabadi, H.; Iranpoor, N.; Shaterian, H. R. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 166, 71-82.
  • 86
    • 48249138908 scopus 로고    scopus 로고
    • 2Si protection with an aminosilane: reference 24g.
    • 2Si protection with an aminosilane: reference 24g.
  • 87
    • 85005706466 scopus 로고
    • and references cited therein
    • (a) Chan, T. H.; Fleming, I. Synthesis 1979, 761-786, and references cited therein.
    • (1979) Synthesis , pp. 761-786
    • Chan, T.H.1    Fleming, I.2
  • 89
    • 48249114267 scopus 로고    scopus 로고
    • TiCl4, SnCl4, ZrCl4, MgBr 2·OEt2, Cu(OTf)2, BF3· OEt2, Yb(OTf)3, MeAlCl2, Me3SiOTf, t-BuMe2SiOTf, Me3SiOTf/DTBMP, and TfOH were investigated
    • 3SiOTf/DTBMP, and TfOH were investigated.
  • 92
    • 48249092538 scopus 로고    scopus 로고
    • The silyl ether tether decomposed rapidly in the presence of TfOH
    • The silyl ether tether decomposed rapidly in the presence of TfOH.
  • 93
    • 48249123007 scopus 로고    scopus 로고
    • 4 at -78°C for 24 h. The lack of product formation in this reaction, combined with the generation of the desired oxasilacycles when tethered allylsilanes containing bulkier groups at the silyl ether connection were employed, confirms that the mechanism of diene formation involves an intramolecular allylation step.
    • 4 at -78°C for 24 h. The lack of product formation in this reaction, combined with the generation of the desired oxasilacycles when tethered allylsilanes containing bulkier groups at the silyl ether connection were employed, confirms that the mechanism of diene formation involves an intramolecular allylation step.
  • 94
    • 59849087060 scopus 로고    scopus 로고
    • Product Subclass 37: β-Silyl Alcohols and the Peterson Reaction
    • Fleming, I, Ed, Georg Thieme Verlag: Stuttgart, Germany, Chapter 4.4.37, pp
    • (a) Ager, D. J. Product Subclass 37: β-Silyl Alcohols and the Peterson Reaction. In Science of Synthesis; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 2002; Vol. 4, Chapter 4.4.37, pp 789-809.
    • (2002) Science of Synthesis , vol.4 , pp. 789-809
    • Ager, D.J.1
  • 95
  • 98
    • 37049096935 scopus 로고    scopus 로고
    • Evidence for a stepwise reaction mechanism in the reaction of allylsilanes with electrophiles: Fleming, I.; Langley, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 1421-1423.
    • Evidence for a stepwise reaction mechanism in the reaction of allylsilanes with electrophiles: Fleming, I.; Langley, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 1421-1423.
  • 100
    • 48249120229 scopus 로고    scopus 로고
    • The energetic barrier to bond rotation will be very low
    • The energetic barrier to bond rotation will be very low.
  • 109
    • 48249156047 scopus 로고    scopus 로고
    • In our work on the synthesis of β-allyl-C-mannosyl derivatives using a related intramolecular allylation strategy, the isolation of intermediates along this mechanistic pathway supports this proposed mechanism: see reference 23e
    • In our work on the synthesis of β-allyl-C-mannosyl derivatives using a related intramolecular allylation strategy, the isolation of intermediates along this mechanistic pathway supports this proposed mechanism: see reference 23e.
  • 111
    • 48249110178 scopus 로고    scopus 로고
    • We do not discount a non-concerted elimination pathway in which ionization first generates an allyl carbocationic intermediate, which then collapses to the diene through loss of the trimethylsilyl group. However, the carbocationic intermediate would again be expected to give rise to an (E)-diene product for similar reasons to those outlined in the text
    • We do not discount a non-concerted elimination pathway in which ionization first generates an allyl carbocationic intermediate, which then collapses to the diene through loss of the trimethylsilyl group. However, the carbocationic intermediate would again be expected to give rise to an (E)-diene product for similar reasons to those outlined in the text.
  • 113
    • 48249112429 scopus 로고    scopus 로고
    • This Lewis acid had shown greatest promise in our early studies with 9aa
    • This Lewis acid had shown greatest promise in our early studies with 9aa.
  • 114
    • 48249106099 scopus 로고    scopus 로고
    • 3 substituent, undergo elimination and provide the source of diene; however, the exclusive formation of the (E)-diene would point against this.
    • 3 substituent, undergo elimination and provide the source of diene; however, the exclusive formation of the (E)-diene would point against this.
  • 115
    • 48249143460 scopus 로고    scopus 로고
    • Diene (E)-27 was not particularly stable; however, in some cases, small amounts of this side product could be isolated by HPLC and at least partially characterized (see the Supporting Information).
    • Diene (E)-27 was not particularly stable; however, in some cases, small amounts of this side product could be isolated by HPLC and at least partially characterized (see the Supporting Information).
  • 126
    • 48249135348 scopus 로고    scopus 로고
    • Analytically pure samples of the allylation products were obtained by HPLC see the Supporting Information
    • Analytically pure samples of the allylation products were obtained by HPLC (see the Supporting Information).
  • 134
    • 48249100725 scopus 로고    scopus 로고
    • The effect of size of the activator on the stereoselectivity of reactions between aldehydes and allylsilanes has also been observed by Denmark, see references 5b and 5c
    • The effect of size of the activator on the stereoselectivity of reactions between aldehydes and allylsilanes has also been observed by Denmark, see references 5b and 5c.
  • 135
    • 48249113193 scopus 로고    scopus 로고
    • Frontier orbital-controlled allylations have also been proposed by Denmark, see reference 25c.
    • Frontier orbital-controlled allylations have also been proposed by Denmark, see reference 25c.
  • 139
    • 0030851176 scopus 로고    scopus 로고
    • This model has also been supported by computational calculations: Bonini, C, Esposito, V, D'Auria, M, Righi, G. Tetrahedron 1997, 53, 13419-13426
    • This model has also been supported by computational calculations: Bonini, C.; Esposito, V.; D'Auria, M.; Righi, G. Tetrahedron 1997, 53, 13419-13426.
  • 143
    • 0035823879 scopus 로고    scopus 로고
    • Certain aluminum Lewis acids have been proposed to form chelates between carbonyl groups and a β-silyl ether functionality: Evans, D. A, Allison, B. D, Yang, M. G, Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840-10852
    • Certain aluminum Lewis acids have been proposed to form chelates between carbonyl groups and a β-silyl ether functionality: Evans, D. A.; Allison, B. D.; Yang, M. G.; Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840-10852.
  • 146
    • 48249083658 scopus 로고    scopus 로고
    • A chelation-control argument cannot be used to rationalize the stereochemical outcome in this example
    • A chelation-control argument cannot be used to rationalize the stereochemical outcome in this example.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.