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Volumn 9, Issue 15, 2007, Pages 2887-2889

Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; GOLD;

EID: 34547168414     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071108n     Document Type: Article
Times cited : (149)

References (55)
  • 6
    • 19944397199 scopus 로고    scopus 로고
    • For recent reviews of enantioselective hydroamination, see: a
    • For recent reviews of enantioselective hydroamination, see: (a) Hultzsch, K. C Org. Biomol. Chem. 2005, 3, 1819.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 1819
    • Hultzsch, K.C.1
  • 37
    • 33746110458 scopus 로고    scopus 로고
    • For recent examples of gold-catalyzed hydroamination, see: a
    • For recent examples of gold-catalyzed hydroamination, see: (a) Liu, X.-Y.; Li, C-H.; Che, C-M. Org. Lett. 2006, 8, 2707.
    • (2006) Org. Lett , vol.8 , pp. 2707
    • Liu, X.-Y.1    Li, C.-H.2    Che, C.-M.3
  • 47
    • 15944427478 scopus 로고    scopus 로고
    • 2 (P-P = bidentate phosphine; X = anionic ligand or counterion), see: (a) Munoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293.
    • 2 (P-P = bidentate phosphine; X = anionic ligand or counterion), see: (a) Munoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293.
  • 50
    • 84858091526 scopus 로고    scopus 로고
    • 4 (5 mol %) in m-xylene at it for 24 h led to no consumption of 2a.
    • 4 (5 mol %) in m-xylene at it for 24 h led to no consumption of 2a.
  • 51
    • 84858107125 scopus 로고    scopus 로고
    • N-Allenyl sulfonamides failed to undergo efficient enantioselective hydroamination under these conditions. For example, reaction of N-(2,2-diphenyl-4,5-hexadienyl)-p-toluenesulfonamide (0.30 M) with a catalytic mixture of, S)-l]Au2Cl2 (2.5 mol , and AgClO4 5 mol , at -20°C for 48 h led to 66% conversion to form 4,4-diphenyl-l-p-toluenesulfonyl-2-vinylpyrrolidine with 8% ee
    • 4 (5 mol %) at -20°C for 48 h led to 66% conversion to form 4,4-diphenyl-l-p-toluenesulfonyl-2-vinylpyrrolidine with 8% ee.
  • 52
    • 34547149600 scopus 로고    scopus 로고
    • An authentic sample of (S)-15 (98% ee) was prepared from commercially available Z-L-prolinol in two steps employing published procedures.14b,c
    • b,c
  • 55
    • 84858107126 scopus 로고    scopus 로고
    • 2 [1:1 (v/v)] in a 10 cm cell displayed an optical rotation of +0.41.
    • 2 [1:1 (v/v)] in a 10 cm cell displayed an optical rotation of +0.41.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.