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Volumn , Issue , 2007, Pages 255-286

Chiral Lewis Bases as Catalysts

Author keywords

Addition of acetylenes; Aldol type reactions; Allenylation; Allylation reactions; Chiral Lewis bases as catalysts; Epoxide opening; Hydrocyanation and isonitrile addition; Propargylation; Reduction of imines

Indexed keywords


EID: 84891036468     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527610945.ch7     Document Type: Chapter
Times cited : (38)

References (182)
  • 3
    • 84891015441 scopus 로고    scopus 로고
    • Organometallics in Synthesis
    • In: Schlosser, M. (Ed.), J. Wiley & Sons, Chichester
    • Marshal, J.A. In: Schlosser, M. (Ed.), Organometallics in Synthesis. J. Wiley & Sons, Chichester, 2002, p. 399.
    • (2002) , pp. 399
    • Marshal, J.A.1
  • 8
    • 0003461511 scopus 로고    scopus 로고
    • Silicon in Organic, Organometallic and Polymeric Chemistry
    • Wiley, New York
    • Brook, M.A., Silicon in Organic, Organometallic and Polymeric Chemistry. Wiley, New York, 2000, pp. 133-136.
    • (2000) , pp. 133-136
    • Brook, M.A.1
  • 15
    • 23044466068 scopus 로고    scopus 로고
    • For a detailed discussion of changing the electronics of the silicon upon extra coordination to Lewis bases, see:
    • For a detailed discussion of changing the electronics of the silicon upon extra coordination to Lewis bases, see: Rendler, S., Oestreich, M., Synthesis 2005, 1727.
    • (2005) Synthesis , pp. 1727
    • Rendler, S.1    Oestreich, M.2
  • 16
    • 0001226919 scopus 로고
    • For the use of stoichiometric, achiral Lewis acids, see, e.g.
    • For the use of stoichiometric, achiral Lewis acids, see, e.g. Kira, M., Kobayashi, M., Sakurai, H., Tetrahedron Lett. 1987, 28, 4081;
    • (1987) Tetrahedron Lett , vol.28 , pp. 4081
    • Kira, M.1    Kobayashi, M.2    Sakurai, H.3
  • 17
    • 0025332409 scopus 로고
    • For an overview of chiral Lewis acids, see Ref. [1].
    • Kira, M., Sato, K., Sakurai, H., J. Am. Chem. Soc. 1990, 112, 257. For an overview of chiral Lewis acids, see Ref. [1].
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 257
    • Kira, M.1    Sato, K.2    Sakurai, H.3
  • 18
    • 0012801796 scopus 로고
    • Allyl trichlorosilane is conveniently prepared from allyl chloride, Cl3SiH, CuCl, and (i-Pr)2EtN (or Et3N) in ether at 20 °C:
    • Allyl trichlorosilane is conveniently prepared from allyl chloride, Cl3SiH, CuCl, and (i-Pr)2EtN (or Et3N) in ether at 20 °C: Kobayashi, S., Nishio, K., Chem. Lett. 1994, 1773;
    • (1994) Chem. Lett , pp. 1773
    • Kobayashi, S.1    Nishio, K.2
  • 19
    • 0034054155 scopus 로고    scopus 로고
    • For an overview of the various other methods, see:
    • Nakajima, M., Saito, M., Hashimoto, S., Chem. Pharm. Bull. 2000, 48, 306. For an overview of the various other methods, see:
    • (2000) Chem. Pharm. Bull , vol.48 , pp. 306
    • Nakajima, M.1    Saito, M.2    Hashimoto, S.3
  • 20
    • 33846964661 scopus 로고    scopus 로고
    • Encyclopedia of Reagents for Organic Synthesis (eEROS)
    • In: Paquette, L.A. (Ed.), J. Wiley & Sons, New York
    • Kocovsky, P. In: Paquette, L.A. (Ed.), Encyclopedia of Reagents for Organic Synthesis (eEROS). J. Wiley & Sons, New York, 2004, RN00568.
    • (2004)
    • Kocovsky, P.1
  • 32
    • 0001579610 scopus 로고
    • Allylsilanes, Allylstannanes and Related Systems
    • For the reaction catalyzed by Lewis acids, see the following:, In: Trost, B.M., Fleming, I. (Eds.), Pergamon, Oxford
    • For the reaction catalyzed by Lewis acids, see the following: Fleming, I. Allylsilanes, Allylstannanes and Related Systems. In: Trost, B.M., Fleming, I. (Eds.), Comprehensive Organic Synthesis. Pergamon, Oxford, 1991, Vol. 2, p. 563.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 563
    • Fleming, I.1
  • 36
    • 0034698174 scopus 로고    scopus 로고
    • For an alternative route, utilizing trans-crotyl chloride, SiCl4, and Cp2Ni in HMPA at 90 °C, see:
    • Shibato, A., Itagaki, Y., Tayama, E., Hokke, Y., Asao, N., Maruoka, K., Tetrahedron 2000, 56, 5373. For an alternative route, utilizing trans-crotyl chloride, SiCl4, and Cp2Ni in HMPA at 90 °C, see:
    • (2000) Tetrahedron , vol.56 , pp. 5373
    • Shibato, A.1    Itagaki, Y.2    Tayama, E.3    Hokke, Y.4    Asao, N.5    Maruoka, K.6
  • 38
    • 44649119573 scopus 로고
    • Yet another alternative, using transcrotyl chloride with Cl3 SiH and Bu4PCl at 150 °C has also been reported:
    • Lefort, M., Simmonet, C., Birot, M., Deleris, G., Dunogues, J., Calas, R., Tetrahedron Lett. 1980, 21, 1857. Yet another alternative, using transcrotyl chloride with Cl3 SiH and Bu4PCl at 150 °C has also been reported:
    • (1980) Tetrahedron Lett , vol.21 , pp. 1857
    • Lefort, M.1    Simmonet, C.2    Birot, M.3    Deleris, G.4    Dunogues, J.5    Calas, R.6
  • 40
    • 0010628946 scopus 로고
    • cis-Crotyl trichlorosilane can be prepared via the 1, 4-addition of Cl3SiH to butadiene, catalyzed by (PhCN)2PdCl2 [10] or(Ph4P)4Pd (at 20 or -78 °C); for the latter catalyst, see Ref. [14c] and the following:
    • cis-Crotyl trichlorosilane can be prepared via the 1, 4-addition of Cl3SiH to butadiene, catalyzed by (PhCN)2PdCl2 [10] or(Ph4P)4Pd (at 20 or -78 °C); for the latter catalyst, see Ref. [14c] and the following: Tsuji, J., Hara, M., Ohno, K., Tetrahedron 1974, 30, 2143;
    • (1974) Tetrahedron , vol.30 , pp. 2143
    • Tsuji, J.1    Hara, M.2    Ohno, K.3
  • 71
    • 84890997082 scopus 로고    scopus 로고
    • Malkov, A.V., Kočovský, P., unpublished results.
    • Malkov, A.V., Kočovský, P., unpublished results.
  • 80
    • 29144437862 scopus 로고    scopus 로고
    • It is pertinent to note that analogues of QUINOX (24) with a substituent next to the N-O group exhibit low reactivity and drastically decreased enantioselectivity, apparently owing to interference of the substituent in the transition state:
    • It is pertinent to note that analogues of QUINOX (24) with a substituent next to the N-O group exhibit low reactivity and drastically decreased enantioselectivity, apparently owing to interference of the substituent in the transition state: Hrdina, R., Stara, I.G., Dufková, L., Mitchell, S., Císařová, I., Kotora, M., Tetrahedron 2006, 62, 968;
    • (2006) Tetrahedron , vol.62 , pp. 968
    • Hrdina, R.1    Stara, I.G.2    Dufková, L.3    Mitchell, S.4    Císařová, I.5    Kotora, M.6
  • 81
    • 84891031374 scopus 로고    scopus 로고
    • Malkov, A.V., Gutnov, A., Kočovský, P., unpublished results.
    • Malkov, A.V., Gutnov, A., Kočovský, P., unpublished results.
  • 84
    • 85190280711 scopus 로고
    • For the Kröhnke annulation, see:, For a review, see:
    • For the Kröhnke annulation, see: Kröhnke, F., Chem. Ber. 1937, 70, 864. For a review, see:
    • (1937) Chem. Ber , vol.70 , pp. 864
    • Kröhnke, F.1
  • 98
    • 11144305011 scopus 로고    scopus 로고
    • For an overview on the allylation of acylhydrazones, using both Lewis acids and bases and chiral auxiliaries, see:
    • Ogawa, C., Sugiura, M., Kobayashi, S., Angew. Chem., Int. Ed. 2004, 43, 6491. For an overview on the allylation of acylhydrazones, using both Lewis acids and bases and chiral auxiliaries, see:
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 6491
    • Ogawa, C.1    Sugiura, M.2    Kobayashi, S.3
  • 105
    • 0000862669 scopus 로고    scopus 로고
    • For a general review on enantioselective additions to imines, see:
    • For a general review on enantioselective additions to imines, see: Kobayashi, S., Chem. Rev. 1999, 99, 1069.
    • (1999) Chem. Rev , vol.99 , pp. 1069
    • Kobayashi, S.1
  • 112
    • 33745941049 scopus 로고    scopus 로고
    • The same catalyst (50) has been employed to facilitate [3+2] cycloadditions:
    • The same catalyst (50) has been employed to facilitate [3+2] cycloadditions: Wilson, J.E., Fu, G., Angew. Chem., Int. Ed. 2006, 45, 1426.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 1426
    • Wilson, J.E.1    Fu, G.2
  • 124
    • 84890982720 scopus 로고    scopus 로고
    • For other approaches, see also Ref. [61b].
    • For other approaches, see also Ref. [61b].
  • 159
    • 4344661511 scopus 로고    scopus 로고
    • For a recent overview on asymmetric cyanation of ketimines, using various Lewis and Brønsted acids, see:
    • For a recent overview on asymmetric cyanation of ketimines, using various Lewis and Brønsted acids, see: Spino, C., Angew. Chem., Int. Ed. 2004, 43, 1764.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 1764
    • Spino, C.1
  • 164
    • 84891001075 scopus 로고    scopus 로고
    • The absolute configuration of the products have not been revealed in Sun's paper (Ref.[79]), but could be deduced, in some instances, from the chiral HPLC data given in the Supporting Information and their comparison with our own experiments (Ref.[80]).
    • The absolute configuration of the products have not been revealed in Sun's paper (Ref.[79]), but could be deduced, in some instances, from the chiral HPLC data given in the Supporting Information and their comparison with our own experiments (Ref.[80]).
  • 182
    • 84890993114 scopus 로고    scopus 로고
    • Malkov, A.V., Kočovský, P., unpublished results.
    • Malkov, A.V., Kočovský, P., unpublished results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.