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Volumn 132, Issue 15, 2010, Pages 5522-5531

Direct catalytic asymmetric addition of allyl cyanide to ketones via soft lewis acid/hard brønsted base/hard lewis base catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ADDITION; BASE CATALYST; CATALYST LOADINGS; CATALYTIC SYSTEM; HIGHER YIELD; LEWIS ACID; LEWIS BASE; MECHANISTIC STUDIES; MOLAR RATIO; PHOSPHINE OXIDE; RATE DETERMINING STEP; REACTION EFFICIENCY; TERTIARY ALCOHOLS;

EID: 77951061383     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101687p     Document Type: Article
Times cited : (102)

References (159)
  • 6
  • 9
    • 0037541354 scopus 로고    scopus 로고
    • For recent reviews of catalytic asymmetric synthesis of tertiary alcohols, see
    • For recent reviews of catalytic asymmetric synthesis of tertiary alcohols, see: Christoffers, J. and Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1688
    • Christoffers, J.1    Baro, A.2
  • 15
    • 57649120956 scopus 로고    scopus 로고
    • For a general and efficient protocol for the synthesis of enantioenriched tertiary alcohols, see
    • For a general and efficient protocol for the synthesis of enantioenriched tertiary alcohols, see: Stymiest, J. L., Bagutski, V., French, R. M., and Aggarwal, V. K. Nature 2008, 456, 778
    • (2008) Nature , vol.456 , pp. 778
    • Stymiest, J.L.1    Bagutski, V.2    French, R.M.3    Aggarwal, V.K.4
  • 30
    • 0032554099 scopus 로고    scopus 로고
    • For selected examples, see: Aryl Zn
    • For selected examples, see: Aryl Zn: Dosa, P. I. and Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 445
    • Dosa, P.I.1    Fu, G.C.2
  • 47
    • 2542622015 scopus 로고    scopus 로고
    • Vinyl Zn
    • Vinyl Zn: Li, H. and Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 6538
  • 68
    • 0037419835 scopus 로고    scopus 로고
    • For examples of catalytic asymmetric addition to ketones incorporated into multicomponent reactions, see
    • For examples of catalytic asymmetric addition to ketones incorporated into multicomponent reactions, see: Cauble, D. F., Gipson, J. D., and Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1110
    • Cauble, D.F.1    Gipson, J.D.2    Krische, M.J.3
  • 73
    • 25444446131 scopus 로고    scopus 로고
    • For examples of catalytic asymmetric addition to ketones coupled with hydrogenation, see
    • For examples of catalytic asymmetric addition to ketones coupled with hydrogenation, see: Lam, H. W. and Joensuu, P. M. Org. Lett. 2005, 7, 4225
    • (2005) Org. Lett. , vol.7 , pp. 4225
    • Lam, H.W.1    Joensuu, P.M.2
  • 83
    • 0001964537 scopus 로고
    • For general reviews of the use of α-cyano carbanions, see
    • For general reviews of the use of α-cyano carbanions, see: Arseniyadis, S., Kyler, K. S., and Watt, D. S. Org. React. 1984, 31, 1
    • (1984) Org. React. , vol.31 , pp. 1
    • Arseniyadis, S.1    Kyler, K.S.2    Watt, D.S.3
  • 87
    • 77951066295 scopus 로고    scopus 로고
    • For catalytic generation of α-cyano carbanions and their integration into subsequent C-C bond-forming processes, see: Proazaphosphatrane catalyst
    • For catalytic generation of α-cyano carbanions and their integration into subsequent C-C bond-forming processes, see: Proazaphosphatrane catalyst
  • 100
    • 0034728564 scopus 로고    scopus 로고
    • For detailed studies of C- and N-bound Pd nitrile nucleophiles, see
    • For detailed studies of C- and N-bound Pd nitrile nucleophiles, see: Naota, T., Tannna, A., and Murahashi, S.-I. J. Am. Chem. Soc. 2000, 122, 2960
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2960
    • Naota, T.1    Tannna, A.2    Murahashi, S.-I.3
  • 102
    • 0037169064 scopus 로고    scopus 로고
    • For examples of the use of allylic cyanides as pronucleophiles in racemic reactions, see
    • For examples of the use of allylic cyanides as pronucleophiles in racemic reactions, see: Kisanga, P. B. and Verkade, J. G. J. Org. Chem. 2002, 67, 426
    • (2002) J. Org. Chem. , vol.67 , pp. 426
    • Kisanga, P.B.1    Verkade, J.G.2
  • 105
    • 33744921636 scopus 로고    scopus 로고
    • For examples of carbocyanation via C-CN bond cleavage of allylic cyanides, see
    • For examples of carbocyanation via C-CN bond cleavage of allylic cyanides, see: Nakao, Y., Yukawa, T., Hirata, Y., Oda, S., Satoh, J., and Hiyama, T. J. Am. Chem. Soc. 2006, 128, 7116
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 7116
    • Nakao, Y.1    Yukawa, T.2    Hirata, Y.3    Oda, S.4    Satoh, J.5    Hiyama, T.6
  • 109
    • 70349931503 scopus 로고    scopus 로고
    • 6/(R, R)-Ph-BPE/LiOAr for the catalytic activation of thioamide pronucleophiles, see
    • 6/(R, R)-Ph-BPE/LiOAr for the catalytic activation of thioamide pronucleophiles, see: Suzuki, Y., Yazaki, R., Kumagai, N., and Shibasaki, M. Angew. Chem., Int. Ed. 2009, 48, 5026
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5026
    • Suzuki, Y.1    Yazaki, R.2    Kumagai, N.3    Shibasaki, M.4
  • 111
    • 0036625219 scopus 로고    scopus 로고
    • For recent reviews of cooperative catalysis, see: Lewis acid/Brønsted base
    • For recent reviews of cooperative catalysis, see: Lewis acid/Brønsted base: Shibasaki, M. and Yoshikawa, N. Chem. Rev. 2002, 102, 2187
    • (2002) Chem. Rev. , vol.102 , pp. 2187
    • Shibasaki, M.1    Yoshikawa, N.2
  • 115
    • 16844374787 scopus 로고    scopus 로고
    • Lewis acid/Brønsted acid and Lewis acid/Lewis acid
    • Lewis acid/Brønsted acid and Lewis acid/Lewis acid: Yamamoto, H. and Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1924
    • Yamamoto, H.1    Futatsugi, K.2
  • 117
    • 77951048001 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 118
    • 0000986218 scopus 로고
    • For formation of CuOAr upon addition of alkali metal aryloxides to Cu(I) salts, see
    • For formation of CuOAr upon addition of alkali metal aryloxides to Cu(I) salts, see: Reichle, W. T. Inorg. Chim. Acta 1971, 5, 325
    • (1971) Inorg. Chim. Acta , vol.5 , pp. 325
    • Reichle, W.T.1
  • 122
    • 0345195964 scopus 로고    scopus 로고
    • For selected examples of catalytic asymmetric C-C or C-B bond formation using copper alkoxides, see
    • For selected examples of catalytic asymmetric C-C or C-B bond formation using copper alkoxides, see: Pagenkopf, B. L., Krüger, J., Stojanovic, A., and Carreira, E. M. Angew. Chem., Int. Ed. 1998, 37, 3124
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3124
    • Pagenkopf, B.L.1    Krüger, J.2    Stojanovic, A.3    Carreira, E.M.4
  • 131
    • 0001623793 scopus 로고
    • For the synthesis, characterization, and application of mesitylcopper, see
    • For the synthesis, characterization, and application of mesitylcopper, see: Tsuda, T., Yazawa, T., Watanabe, K., Fujii, T., and Saegusa, T. J. Org. Chem. 1981, 46, 192
    • (1981) J. Org. Chem. , vol.46 , pp. 192
    • Tsuda, T.1    Yazawa, T.2    Watanabe, K.3    Fujii, T.4    Saegusa, T.5
  • 134
    • 77951076530 scopus 로고    scopus 로고
    • 4- p -OMe. 1a would not be involved in the catalyst turnover step
    • 4- p -OMe. 1a would not be involved in the catalyst turnover step.
  • 135
    • 0030529861 scopus 로고    scopus 로고
    • Coordination in an end-on fashion has been generally proposed for nitriles. See
    • Coordination in an end-on fashion has been generally proposed for nitriles. See: Michelin, R. A., Mozzon, M., and Bertani, R. Coord. Chem. Rev. 1996, 147, 299
    • (1996) Coord. Chem. Rev. , vol.147 , pp. 299
    • Michelin, R.A.1    Mozzon, M.2    Bertani, R.3
  • 137
    • 0001389517 scopus 로고    scopus 로고
    • For selected examples of side-on coordination of nitriles to transition metals, see
    • For selected examples of side-on coordination of nitriles to transition metals, see: Thomas, S. and Young, C. G. Organometallics 1998, 17, 182
    • (1998) Organometallics , vol.17 , pp. 182
    • Thomas, S.1    Young, C.G.2
  • 142
    • 77951053407 scopus 로고    scopus 로고
    • 4- p -OMe) resulted in lower enantioselectivity (76% yield, 96% ee for Na and 87% yield, 85% ee for K under reaction conditions otherwise identical to those for entry 2)
    • 4- p -OMe) resulted in lower enantioselectivity (76% yield, 96% ee for Na and 87% yield, 85% ee for K under reaction conditions otherwise identical to those for entry 2).
  • 143
    • 77951041795 scopus 로고    scopus 로고
    • 4- p -OMe) in the presence of a hard Lewis base (entries 3-7) originates from the dissociation of this relatively stable tetramer cannot be ruled out.
    • 4- p -OMe) in the presence of a hard Lewis base (entries 3-7) originates from the dissociation of this relatively stable tetramer cannot be ruled out.
  • 145
    • 28444457008 scopus 로고    scopus 로고
    • references cited therein For selected examples of Lewis base activation of Brønsted bases, see
    • references cited therein For selected examples of Lewis base activation of Brønsted bases, see: McGrath, M. J. and OBrien, P. J. Am. Chem. Soc. 2005, 127, 16378
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 16378
    • McGrath, M.J.1    Obrien, P.2
  • 148
    • 35948934624 scopus 로고    scopus 로고
    • Enhanced Lewis basicity of LiOPh was observed by using bidentate bis(phosphine oxide) 4 in Mukaiyama aldol reactions. X-ray crystallographic analysis proved the coordination of 4 to the Li cation in a bidentate fashion. See
    • Enhanced Lewis basicity of LiOPh was observed by using bidentate bis(phosphine oxide) 4 in Mukaiyama aldol reactions. X-ray crystallographic analysis proved the coordination of 4 to the Li cation in a bidentate fashion. See: Hatano, M., Takagi, E., and Ishihara, K. Org. Lett. 2007, 9, 4527
    • (2007) Org. Lett. , vol.9 , pp. 4527
    • Hatano, M.1    Takagi, E.2    Ishihara, K.3
  • 149
    • 77951073100 scopus 로고    scopus 로고
    • 4- p -OMe) as the Brønsted base (63% yield, 98% ee for Na and 57% yield, 98% ee for K under reaction conditions otherwise identical to those of entry 6)
    • 4- p -OMe) as the Brønsted base (63% yield, 98% ee for Na and 57% yield, 98% ee for K under reaction conditions otherwise identical to those of entry 6).
  • 150
    • 29944440585 scopus 로고    scopus 로고
    • For an example of a Cu(I) complex coordinated with both phosphine and phosphine oxide, see
    • For an example of a Cu(I) complex coordinated with both phosphine and phosphine oxide, see: Coté, A. and Charette, A. B. J. Org. Chem. 2005, 70, 10864
    • (2005) J. Org. Chem. , vol.70 , pp. 10864
    • Coté, A.1    Charette, A.B.2
  • 151
    • 33646069977 scopus 로고    scopus 로고
    • For 1,3-transposition of allylic metal species, see:, and references therein
    • For 1,3-transposition of allylic metal species, see: Sklute, G. and Marek, I. J. Am. Chem. Soc. 2006, 128, 4642 and references therein
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4642
    • Sklute, G.1    Marek, I.2
  • 152
    • 77951083334 scopus 로고    scopus 로고
    • Details of the X-ray analysis are described in the Supporting Information
    • Details of the X-ray analysis are described in the Supporting Information.
  • 153
    • 77951084710 scopus 로고    scopus 로고
    • The possibility that oligomeric homochiral and heterochiral complexes exhibit similar reactivity and enantioselectivity to afford the linear relationship cannot be ruled out
    • The possibility that oligomeric homochiral and heterochiral complexes exhibit similar reactivity and enantioselectivity to afford the linear relationship cannot be ruled out.
  • 154
    • 0032538773 scopus 로고    scopus 로고
    • For recent comprehensive reviews of nonlinear effects in asymmetric catalysis, see
    • For recent comprehensive reviews of nonlinear effects in asymmetric catalysis, see: Girard, C. and Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2922
    • Girard, C.1    Kagan, H.B.2
  • 157
    • 77951066975 scopus 로고    scopus 로고
    • In the reaction with β- or γ-substituted allylic cyanides under the optimized reaction conditions, the desired products were not detected. The steric factor on the allylic cyanide is assumed to be critical in preventing the addition to ketones, possibly because of increased steric demands at the transition state
    • In the reaction with β- or γ-substituted allylic cyanides under the optimized reaction conditions, the desired products were not detected. The steric factor on the allylic cyanide is assumed to be critical in preventing the addition to ketones, possibly because of increased steric demands at the transition state.


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