메뉴 건너뛰기




Volumn 48, Issue 7, 2009, Pages 1313-1316

Organocatalytic asymmetric alkylation of aldehydes by SNreaction of alcohols

Author keywords

Alcohols; Aldehydes; Carbocations; Enamines; Organocatalysis

Indexed keywords

ALDEHYDES; ALKYLATION; AMINES; CATALYSIS; CHEMICAL REACTIONS; FOURIER TRANSFORMS; HYDROCARBONS; RATE CONSTANTS; REACTION KINETICS;

EID: 60149108649     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805423     Document Type: Article
Times cited : (242)

References (86)
  • 1
    • 33750507943 scopus 로고    scopus 로고
    • For recent reports of catalyzed C-C, C-N, and C-O bond formation through direct substitution of allylic or propargylic alcohols with nucleophiles, see: a
    • For recent reports of catalyzed C-C, C-N, and C-O bond formation through direct substitution of allylic or propargylic alcohols with nucleophiles, see: a) V. Terrasson, S. Marque, J.-M. Campagne, D. Prim, Adv. Synth. Catal. 2006, 348, 2063;
    • (2006) Adv. Synth. Catal , vol.348 , pp. 2063
    • Terrasson, V.1    Marque, S.2    Campagne, J.-M.3    Prim, D.4
  • 16
    • 60149086735 scopus 로고    scopus 로고
    • For valuable transformations on water or in the presence of water, see: a a C.-J. Li, T.-H. Chan, Organic Reaction in Aqueous Media, Wiley, New York, 1997;
    • For valuable transformations "on water" or "in the presence of water", see: a a) C.-J. Li, T.-H. Chan, Organic Reaction in Aqueous Media, Wiley, New York, 1997;
  • 17
    • 60149103075 scopus 로고    scopus 로고
    • Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998;
    • b) Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998;
  • 18
    • 24044470646 scopus 로고    scopus 로고
    • c) C.-J. Li, Chem. Rev. 2005, 105, 3095;
    • (2005) Chem. Rev , vol.105 , pp. 3095
    • Li, C.-J.1
  • 20
    • 60149102858 scopus 로고    scopus 로고
    • Organic Reaction in Water (Ed.: U. M. Lindström), Blackwell Publishing, Oxford, 2007;
    • e)Organic Reaction in Water (Ed.: U. M. Lindström), Blackwell Publishing, Oxford, 2007;
  • 26
    • 60149087986 scopus 로고    scopus 로고
    • Chem. Int. Ed. 2005, 44, 3157.
    • (2005) Chem. Int. Ed , vol.44 , pp. 3157
  • 38
  • 56
    • 0345825852 scopus 로고    scopus 로고
    • For the first nucleophilic substitution proceeding under enamine catalysis, see: a
    • For the first nucleophilic substitution proceeding under enamine catalysis, see: a) N. Vignola, B. List, J. Am. Chem. Soc. 2004, 126, 450;
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 450
    • Vignola, N.1    List, B.2
  • 58
    • 34848814187 scopus 로고    scopus 로고
    • For organocatalytic domino reactions consisting of a Michael addition and subsequent intramolecular a alkylation, see: c H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886;
    • For organocatalytic domino reactions consisting of a Michael addition and subsequent intramolecular a alkylation, see: c) H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886;
  • 63
    • 53349122064 scopus 로고    scopus 로고
    • Recently, MacMillan reported an interesting methodology for highly enantioselective alkylation of aldehydes by photochemical activation of α-carbonyl compounds, see
    • Recently, MacMillan reported an interesting methodology for highly enantioselective alkylation of aldehydes by photochemical activation of α-carbonyl compounds, see: D. A. Nice-wicz, D. W. C. MacMillan, Science 2008, 322, 77.
    • (2008) Science , vol.322 , pp. 77
    • Nice-wicz, D.A.1    MacMillan, D.W.C.2
  • 64
    • 85200105936 scopus 로고    scopus 로고
    • The SOMO activation, developed by MacMillan and co-workers, is also another important strategy for the α-alkylation of aldehydes: T. D. Beeson, A. Mastracchio, J. Hong, K. Ashton, D. W. C. MacMillan, Science 2007, 316, 582.
    • The SOMO activation, developed by MacMillan and co-workers, is also another important strategy for the α-alkylation of aldehydes: T. D. Beeson, A. Mastracchio, J. Hong, K. Ashton, D. W. C. MacMillan, Science 2007, 316, 582.
  • 69
    • 33845183755 scopus 로고    scopus 로고
    • The 4,4′-bis(dimethylamino)diphenylmethane carbocation has a half-life of 10-20 seconds; see: R. A. McCLelland, V. M. Kana-gasabapathy, N. S. Banait, S. J. Steenken, J. Am. Chem. Soc. 1989, 111, 3966.
    • The 4,4′-bis(dimethylamino)diphenylmethane carbocation has a half-life of 10-20 seconds; see: R. A. McCLelland, V. M. Kana-gasabapathy, N. S. Banait, S. J. Steenken, J. Am. Chem. Soc. 1989, 111, 3966.
  • 70
    • 33745715054 scopus 로고    scopus 로고
    • and references therein. For theoretical investigations, see
    • G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79, and references therein. For theoretical investigations, see:
    • (2006) Aldrichimica Acta , vol.39 , pp. 79
    • Lelais, G.1    MacMillan, D.W.C.2
  • 73
    • 60149092084 scopus 로고    scopus 로고
    • The major diastereoisomer and the absolute configuration obtained in the reaction using ferrocenyl alcohol 4 were assigned on the basis of: a The reaction of alcohol (S)-4 with racemic G occurrs with retention of configuration;
    • The major diastereoisomer and the absolute configuration obtained in the reaction using ferrocenyl alcohol 4 were assigned on the basis of: a) The reaction of alcohol (S)-4 with racemic G occurrs with retention of configuration;
  • 74
    • 60149090650 scopus 로고    scopus 로고
    • The major diastereo-isomer obtained with racemic or optically active alcohol 4 is the same;
    • b) The major diastereo-isomer obtained with racemic or optically active alcohol 4 is the same;
  • 75
    • 60149103573 scopus 로고    scopus 로고
    • The optically active catalyst G affords products having an S configuration at C2. For the proposed model, see the Supporting Information.
    • c) The optically active catalyst G affords products having an S configuration at C2. For the proposed model, see the Supporting Information.
  • 77
    • 38349147664 scopus 로고    scopus 로고
    • For reactions in which 3-(1arylsulfonylalkyl)indoles are used as suitable electrophilic precursors, see
    • a) For reactions in which 3-(1arylsulfonylalkyl)indoles are used as suitable electrophilic precursors, see: R. Ballini, A. Palmieri, M. Petrini, R. R. Shaikh, Adv. Synth. Catal. 2008, 350, 129;
    • (2008) Adv. Synth. Catal , vol.350 , pp. 129
    • Ballini, R.1    Palmieri, A.2    Petrini, M.3    Shaikh, R.R.4
  • 82
    • 60149103074 scopus 로고    scopus 로고
    • Alcohol 5 provided little control in the diastereoselection, which is probably caused by the fast reaction of the carbocation formed under the reaction conditions. The simple stereoselection of our reaction was different from what was obtained by Petrini and Melchiorre et al.: see reference [12].
    • Alcohol 5 provided little control in the diastereoselection, which is probably caused by the fast reaction of the carbocation formed under the reaction conditions. The simple stereoselection of our reaction was different from what was obtained by Petrini and Melchiorre et al.: see reference [12].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.