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Volumn 13, Issue 26, 2007, Pages 7280-7286

Enantioselective radical cyclizations: A new approach to stereocontrol of cascade reactions

Author keywords

Cascade reactions; Enantioselectivity; Lewis acids; Oxime ether; Radicals

Indexed keywords

ENANTIOSELECTIVITY; ESTERS; REACTION KINETICS;

EID: 34548802989     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700864     Document Type: Article
Times cited : (56)

References (116)
  • 1
    • 0004269715 scopus 로고    scopus 로고
    • Vols, and 2 Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
    • a) Radicals in Organic Synthesis, Vols. 1 and 2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001;
    • (2001) Radicals in Organic Synthesis , vol.1
  • 5
    • 14744278476 scopus 로고    scopus 로고
    • For selected examples of enantioselective radical addition reactions and allylations, see: a
    • For selected examples of enantioselective radical addition reactions and allylations, see: a) M. P. Sibi, G. Petrovic, J. Zimmerman, J. Am. Chem. Soc. 2005, 127, 2390;
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 2390
    • Sibi, M.P.1    Petrovic, G.2    Zimmerman, J.3
  • 7
  • 13
    • 33748536687 scopus 로고    scopus 로고
    • For selected examples of enantioselective hydrogen-atom-transfer reactions, see: a
    • For selected examples of enantioselective hydrogen-atom-transfer reactions, see: a) M. P. Sibi, K. Patil, Angew. Chem. 2004, 116, 1255;
    • (2004) Angew. Chem , vol.116 , pp. 1255
    • Sibi, M.P.1    Patil, K.2
  • 14
  • 16
  • 18
    • 0036015090 scopus 로고    scopus 로고
    • For selective examples of enantioselective reductions with chiral hydrogen-atom-transfer reagents, see: a Y. Cai, B. P. Roberts, D. A. Tocher, J. Chem. Soc. Perkin Trans. 1 2002, 1376;
    • For selective examples of enantioselective reductions with chiral hydrogen-atom-transfer reagents, see: a) Y. Cai, B. P. Roberts, D. A. Tocher, J. Chem. Soc. Perkin Trans. 1 2002, 1376;
  • 23
    • 0001635598 scopus 로고    scopus 로고
    • For general information details for enantioselective radical reactions, see: a
    • For general information details for enantioselective radical reactions, see: a) P. Renaud, M. Gerster, Angew. Chem. 1998, 110, 2704;
    • (1998) Angew. Chem , vol.110 , pp. 2704
    • Renaud, P.1    Gerster, M.2
  • 24
  • 31
  • 33
  • 35
    • 0033486022 scopus 로고    scopus 로고
    • Transfer of chirality in radical cyclization was reported. See
    • Transfer of chirality in radical cyclization was reported. See: D. P. Curran, W. Liu, C. H.-T. Chen, J. Am. Chem. Soc. 1999, 121, 11012.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 11012
    • Curran, D.P.1    Liu, W.2    Chen, C.H.-T.3
  • 37
  • 46
  • 49
  • 51
  • 55
  • 57
  • 59
  • 62
    • 15444364760 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1075.
    • (2005) Chem. Int. Ed , vol.44 , pp. 1075
    • Angew1
  • 63
    • 0000457447 scopus 로고
    • For selected examples of tandem or cascade reaction involving radical and ionic processes, see: a
    • For selected examples of tandem or cascade reaction involving radical and ionic processes, see: a) K. Nozaki, K. Oshima, K. Utimoto, Tetrahedron Lett. 1988, 29, 1041;
    • (1988) Tetrahedron Lett , vol.29 , pp. 1041
    • Nozaki, K.1    Oshima, K.2    Utimoto, K.3
  • 70
    • 25844449049 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6190.
    • (2005) Chem. Int. Ed , vol.44 , pp. 6190
    • Angew1
  • 72
    • 33748547632 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5863.
    • (2006) Chem. Int. Ed , vol.45 , pp. 5863
    • Angew1
  • 77
    • 33748225421 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. Engl. 1996, 35, 190; see also reference [5a].
    • Angew. Chem. Int. Ed. Engl. 1996, 35, 190; see also reference [5a].
  • 80
    • 0036250217 scopus 로고    scopus 로고
    • The radical reactions were initiated with triethylborane and oxygen. For reviews on alkylborane, see: a
    • The radical reactions were initiated with triethylborane and oxygen. For reviews on alkylborane, see: a) H. Yorimitsu, H. Shinokubo, K. Oshima, Synlett 2002, 674;
    • (2002) Synlett , pp. 674
    • Yorimitsu, H.1    Shinokubo, H.2    Oshima, K.3
  • 82
    • 0001750953 scopus 로고    scopus 로고
    • N. A. Porter, J. H. L. Wu, G. R. Zhang, A. D. Reed, J. Org. Chem. 1997, 62, 6702; see also references [2b,f].
    • N. A. Porter, J. H. L. Wu, G. R. Zhang, A. D. Reed, J. Org. Chem. 1997, 62, 6702; see also references [2b,f].
  • 83
    • 33751499942 scopus 로고
    • For discussions on atom-transfer cyclization, see: a
    • For discussions on atom-transfer cyclization, see: a) D. P. Curran, J. Tamine, J. Org. Chem. 1991, 56, 2746;
    • (1991) J. Org. Chem , vol.56 , pp. 2746
    • Curran, D.P.1    Tamine, J.2
  • 89
    • 0032837567 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: a) T. Naito, Heterocycles 1999, 50, 505;
    • (1999) Heterocycles , vol.50 , pp. 505
    • Naito, T.1
  • 93
    • 0000657404 scopus 로고    scopus 로고
    • For some examples of the radical reaction of oxime ethers, see: a
    • For some examples of the radical reaction of oxime ethers, see: a) G. K. Friestad, Org. Lett. 1999,1, 1499;
    • (1999) Org. Lett , vol.1 , pp. 1499
    • Friestad, G.K.1
  • 102
    • 0000817491 scopus 로고
    • For some examples of the intermolecular radical addition to imines, see: a
    • For some examples of the intermolecular radical addition to imines, see: a) D. J. Hart, F.L. Seely, J. Am. Chem. Soc. 1988, 110, 1633;
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 1633
    • Hart, D.J.1    Seely, F.L.2
  • 109
    • 24044519216 scopus 로고    scopus 로고
    • Recently, Friestad's and our groups independently reported asymmetric intermolecular radical addition to imines. See: a
    • Recently, Friestad's and our groups independently reported asymmetric intermolecular radical addition to imines. See: a) G. K. Friestad, Y. Shen, E. L. Ruggles, Angew. Chem. 2003, 115, 5215;
    • (2003) Angew. Chem , vol.115 , pp. 5215
    • Friestad, G.K.1    Shen, Y.2    Ruggles, E.L.3
  • 110
  • 114
    • 0037999838 scopus 로고    scopus 로고
    • The radical addition-cyclization of the moiety was achieved in our previous studies, although the reactivity of a resonance-stabilized radical, generated by the initial addition of alkyl radical to acrylate, toward oxime ether is low. See: a
    • The radical addition-cyclization of the moiety was achieved in our previous studies, although the reactivity of a resonance-stabilized radical, generated by the initial addition of alkyl radical to acrylate, toward oxime ether is low. See: a) H. Miyabe, M. Ueda, K. Fujii, A. Nishimura, T. Naito, J. Org. Chem. 2003, 68, 5618;
    • (2003) J. Org. Chem , vol.68 , pp. 5618
    • Miyabe, H.1    Ueda, M.2    Fujii, K.3    Nishimura, A.4    Naito, T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.