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Volumn 50, Issue 5, 2011, Pages 1080-1083

Synthesis of highly enantioenriched C-TERTIARY amines from boronic esters: Application to the synthesis of igmesine

Author keywords

azides; boronic esters; C tertiary amines; quaternary stereocenters; trifluoroborates

Indexed keywords

AZIDES; BORONIC ESTERS; QUATERNARY STEREOCENTERS; TERTIARY AMINE; TRIFLUOROBORATES;

EID: 79251562484     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006037     Document Type: Article
Times cited : (65)

References (77)
  • 1
    • 79251585287 scopus 로고    scopus 로고
    • For recent examples see
    • For recent examples see
  • 17
    • 36148970839 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8468-8470
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8468-8470
  • 22
    • 41249092756 scopus 로고    scopus 로고
    • See also Ref. [1i].
    • Angew. Chem. Int. Ed. 2008, 47, 1176-1178; See also Ref. [1i].
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 1176-1178
  • 26
    • 22744434029 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4627-4631
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4627-4631
  • 28
    • 35048826146 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7704-7707
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7704-7707
  • 30
    • 34547155080 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5565-5567
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5565-5567
  • 38
    • 77954850632 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 5142-5145
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 5142-5145
  • 42
    • 79251543687 scopus 로고    scopus 로고
    • For conversions of boronic esters into amines through borinic esters see
    • For conversions of boronic esters into amines through borinic esters see
  • 46
    • 79251571803 scopus 로고    scopus 로고
    • For aminations of dichloroboranes see
    • For aminations of dichloroboranes see
  • 47
    • 0010603342 scopus 로고
    • For conversions of diaminoboranes into dichloroboranes followed by aminations see
    • H. C. Brown, M. M. Midland, A. B. Levy, J. Am. Chem. Soc. 1973, 95, 2394-2396. For conversions of diaminoboranes into dichloroboranes followed by aminations see
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2394-2396
    • Brown, H.C.1    Midland, M.M.2    Levy, A.B.3
  • 48
    • 0001780025 scopus 로고
    • For one-pot conversions of boronic esters into dichloroboranes followed by aminations see
    • P. Y. Chavant, F. Lhermitte, M. Vaultier, Synlett 1993, 519-521. For one-pot conversions of boronic esters into dichloroboranes followed by aminations see
    • (1993) Synlett , pp. 519-521
    • Chavant, P.Y.1    Lhermitte, F.2    Vaultier, M.3
  • 52
    • 79251560365 scopus 로고    scopus 로고
    • For aminations of trifluoroborate salts see
    • For aminations of trifluoroborate salts see
  • 55
  • 58
    • 70350442360 scopus 로고    scopus 로고
    • Attempted one-pot amination of the simplest tertiary boronic ester 2aa according to Ref. [6e] gave the desired amine but only in moderate yield (50a%), whereas subjecting the trifluoroborate salt 3aa to Matteson's original protocol afforded amine 5aaa in considerably higher yield (74a%). Furthermore, any trifluoroborate salt is readily available from the respective pinacolboronic ester in essentially quantitative yield.
    • Attempted one-pot amination of the simplest tertiary boronic ester 2aa according to Ref. [6e] gave the desired amine but only in moderate yield (50a%), whereas subjecting the trifluoroborate salt 3aa to Matteson's original protocol afforded amine 5aaa in considerably higher yield (74a%). Furthermore, any trifluoroborate salt is readily available from the respective pinacolboronic ester in essentially quantitative yield:, V. Bagutski, A. Ros, V. K. Aggarwal, Tetrahedron 2009, 65, 9956-9960.
    • (2009) Tetrahedron , vol.65 , pp. 9956-9960
    • Bagutski, V.1    Ros, A.2    Aggarwal, V.K.3
  • 59
    • 33751500494 scopus 로고
    • Toluene was the original solvent but we have found 1,2-dichloroethane to be the solvent of choice. For the use of DCE in aminations of dichloroboranes see also.
    • Toluene was the original solvent but we have found 1,2-dichloroethane to be the solvent of choice. For the use of DCE in aminations of dichloroboranes see also:, H. C. Brown, A. M. Salunkhe, B. Singaram, J. Org. Chem. 1991, 56, 1170-1175.
    • (1991) J. Org. Chem. , vol.56 , pp. 1170-1175
    • Brown, H.C.1    Salunkhe, A.M.2    Singaram, B.3
  • 60
    • 79251544932 scopus 로고    scopus 로고
    • For the preparation of the title trifluoroborate and its subsequent amination see Supporting Information
    • For the preparation of the title trifluoroborate and its subsequent amination see Supporting Information.
  • 61
    • 24144470458 scopus 로고    scopus 로고
    • For an example for chemoselective debenzylation see also
    • T. Suzuki, Y. Honda, K. Izawa, R. M. Williams, J. Org. Chem. 2005, 70, 7317-7323. For an example for chemoselective debenzylation see also
    • (2005) J. Org. Chem. , vol.70 , pp. 7317-7323
    • Suzuki, T.1    Honda, Y.2    Izawa, K.3    Williams, R.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.