메뉴 건너뛰기




Volumn 20, Issue 50, 2014, Pages 16478-16483

Highly Enantioselective Ring-Opening Reactions of Aziridines with Indole and Its Application in the Building of C3-Halogenated Pyrroloindolines

Author keywords

asymmetric synthesis; cyclization; magnesium; ring opening reactions

Indexed keywords

ENANTIOSELECTIVITY; HALOGENATION; LIGANDS; MAGNESIUM; POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 84921291238     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404354     Document Type: Article
Times cited : (52)

References (161)
  • 5
    • 84954245298 scopus 로고    scopus 로고
    • 1c
    • 1c Angew. Chem. 2004, 116, 560;
    • (2004) Angew. Chem. , vol.116 , pp. 560
  • 10
    • 84956872036 scopus 로고    scopus 로고
    • Angew. Chem. 2001, 113, 164;
    • (2001) Angew. Chem. , vol.113 , pp. 164
  • 17
    • 1542382740 scopus 로고    scopus 로고
    • Angew. Chem. 2003, 115, 5105;
    • (2003) Angew. Chem. , vol.115 , pp. 5105
  • 24
    • 53249096986 scopus 로고    scopus 로고
    • Angew. Chem. 2008, 120, 603;
    • (2008) Angew. Chem. , vol.120 , pp. 603
  • 26
    • 56449087939 scopus 로고    scopus 로고
    • Angew. Chem. 2008, 120, 4080;
    • (2008) Angew. Chem. , vol.120 , pp. 4080
  • 28
    • 73349095277 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 3396;
    • (2009) Angew. Chem. , vol.121 , pp. 3396
  • 31
    • 81255128912 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 6740;
    • (2011) Angew. Chem. , vol.123 , pp. 6740
  • 36
    • 85023187008 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 2546;
    • (2013) Angew. Chem. , vol.125 , pp. 2546
  • 38
    • 84956950296 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 3332;
    • (2013) Angew. Chem. , vol.125 , pp. 3332
  • 40
    • 84956911654 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 14271.
    • (2013) Angew. Chem. , vol.125 , pp. 14271
  • 48
    • 84918814135 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 7629;
    • (2007) Angew. Chem. , vol.119 , pp. 7629
  • 57
    • 84956943527 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 5661;
    • (2007) Angew. Chem. , vol.119 , pp. 5661
  • 60
    • 84917744167 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 2081;
    • (2013) Angew. Chem. , vol.125 , pp. 2081
  • 62
    • 84956937149 scopus 로고    scopus 로고
    • For selected examples of the asymmetric allylic alkylation of indoles
    • For selected examples of the asymmetric allylic alkylation of indoles:
  • 70
    • 75749091019 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 7981;
    • (2009) Angew. Chem. , vol.121 , pp. 7981
  • 72
    • 77953923919 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 9697;
    • (2009) Angew. Chem. , vol.121 , pp. 9697
  • 78
    • 85042301321 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 4301.
    • (2013) Angew. Chem. , vol.125 , pp. 4301
  • 81
    • 84915776615 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 13598.
    • (2013) Angew. Chem. , vol.125 , pp. 13598
  • 83
    • 33845639797 scopus 로고    scopus 로고
    • Angew. Chem. 2004, 116, 86;
    • (2004) Angew. Chem. , vol.116 , pp. 86
  • 90
    • 84956895703 scopus 로고    scopus 로고
    • For recent reviews on the asymmetric construction of pyrroloindolines
    • For recent reviews on the asymmetric construction of pyrroloindolines:
  • 94
    • 84904477742 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 46;
    • (2012) Angew. Chem. , vol.124 , pp. 46
  • 96
    • 84918791559 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 12834.
    • (2012) Angew. Chem. , vol.124 , pp. 12834
  • 97
    • 84956887697 scopus 로고    scopus 로고
    • For selected examples, see
    • For selected examples, see:
  • 101
    • 0030052741 scopus 로고    scopus 로고
    • for selected examples of ring-opening reaction of enantioenriched aziridines with indoles, see
    • J. querra, C. Pedregal, C. Lamas, Tetrahedron Lett. 1996, 37, 683; for selected examples of ring-opening reaction of enantioenriched aziridines with indoles, see:
    • (1996) Tetrahedron Lett. , vol.37 , pp. 683
    • Querra, J.1    Pedregal, C.2    Lamas, C.3
  • 104
    • 84956906047 scopus 로고    scopus 로고
    • Angew. Chem. 2004, 116, 5456;
    • (2004) Angew. Chem. , vol.116 , pp. 5456
  • 106
    • 38649091963 scopus 로고    scopus 로고
    • for an elegant high regioselectivity and enantiospecificity ring-opening reaction of enantioenriched aziridines with indoles
    • Y. Li, E. Haymanb, M. Plesescua, S. R. Prakash, Tetrahedron Lett. 2008, 49, 1480; for an elegant high regioselectivity and enantiospecificity ring-opening reaction of enantioenriched aziridines with indoles:
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1480
    • Li, Y.1    Haymanb, E.2    Plesescua, M.3    Prakash, S.R.4
  • 108
    • 84956956474 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 9980.
    • (2012) Angew. Chem. , vol.124 , pp. 9980
  • 113
    • 84956912326 scopus 로고    scopus 로고
    • For selected examples of desymmetrization reactions of aziridines
    • For selected examples of desymmetrization reactions of aziridines:
  • 118
    • 70349122350 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 4943;
    • (2009) Angew. Chem. , vol.121 , pp. 4943
  • 127
    • 84896779121 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 6871;
    • (2013) Angew. Chem. , vol.125 , pp. 6871
  • 129
    • 85013239060 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 7641;
    • (2012) Angew. Chem. , vol.124 , pp. 7641
  • 131
    • 84956888778 scopus 로고    scopus 로고
    • See the Supporting Information for the results of a preliminary screening of aziridines. There are limited works on the desymmetrization of this type aziridine
    • See the Supporting Information for the results of a preliminary screening of aziridines. There are limited works on the desymmetrization of this type aziridine:
  • 138
    • 84956894608 scopus 로고    scopus 로고
    • Achiral ligand L9 is beneficial to part of the reaction's scope, and the addition of L9 might also decrease ee values for some substrates
    • Achiral ligand L9 is beneficial to part of the reaction's scope, and the addition of L9 might also decrease ee values for some substrates.
  • 139
    • 85099672121 scopus 로고    scopus 로고
    • 3-halogenated-pyrroloindolines
    • 3-halogenated-pyrroloindolines:
  • 141
    • 84942827650 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 13162;
    • (2013) Angew. Chem. , vol.125 , pp. 13162
  • 143
    • 84922781616 scopus 로고    scopus 로고
    • 3-halogenated-pyrroloindolines in synthetic chemistry
    • 3-halogenated-pyrroloindolines in synthetic chemistry:
    • (2011) Angew. Chem. , vol.123 , pp. 8255
  • 145
    • 84956930657 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 9371;
    • (2013) Angew. Chem. , vol.125 , pp. 9371
  • 147
    • 83155175212 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 9829;
    • (2011) Angew. Chem. , vol.123 , pp. 9829
  • 150
    • 85099672527 scopus 로고    scopus 로고
    • 3-fluorinated-, chlorinated-, and brominated-pyrroloindolines.
    • 3-fluorinated-, chlorinated-, and brominated-pyrroloindolines.
  • 151
    • 84956906655 scopus 로고    scopus 로고
    • For selected examples, see
    • For selected examples, see:
  • 158
    • 84956960115 scopus 로고    scopus 로고
    • We have tried to examine the ESI-mass spectrum or X-ray crystal analysis for the complexes A-C; however, we could not observe these complexes which might due to the instability of these in situ generated complexes. For these types of in situ generated complexes were also hard to observe in many previous studies, for selected examples, see: ref. [12c] and
    • We have tried to examine the ESI-mass spectrum or X-ray crystal analysis for the complexes A-C; however, we could not observe these complexes which might due to the instability of these in situ generated complexes. For these types of in situ generated complexes were also hard to observe in many previous studies, for selected examples, see: ref. [12c] and


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.