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Volumn 74, Issue 24, 2009, Pages 9274-9279

Enantioselective intramolecular oxidative aminocarbonylation of alkenylureas catalyzed by palladium-spiro bis(isoxazoline) complexes

Author keywords

[No Author keywords available]

Indexed keywords

A-CARBON; CARBON-CARBON DOUBLE BONDS; CHEMICAL EQUATIONS; COORDINATION ABILITY; COORDINATION SITES; DONOR ABILITY; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; ISOXAZOLINES; NITROGEN NUCLEOPHILES; OPTICALLY ACTIVE FORM; PALLADIUM CATALYST; STRUCTURAL CHARACTERISTICS;

EID: 73149098957     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901778a     Document Type: Article
Times cited : (83)

References (87)
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    • For a recent review, see: a
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    • Tamaru and co-workers extensively studied the corresponding none-nantioselective Pd-catalyzed oxidative aminocarbonylation of alkenyl amines. See: (a) Tamaru, Y, Kobayashi, T, Kawamura, S, Ochiai, H, Yoshida, Z. Tetrahedron Lett. 1985, 26, 4479-4482
    • Tamaru and co-workers extensively studied the corresponding none-nantioselective Pd-catalyzed oxidative aminocarbonylation of alkenyl amines. See: (a) Tamaru, Y.; Kobayashi, T.; Kawamura, S.; Ochiai, H.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 4479-4482.
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    • 0037224295 scopus 로고    scopus 로고
    • Organocatalysts has also been used in the preparation of optically active homoproline derivatives, see: a
    • Organocatalysts has also been used in the preparation of optically active homoproline derivatives, see: (a) Takasu, K.; Maiti, S.; Ihara, M. Heterocycles 2003, 59, 51-55.
    • (2003) Heterocycles , vol.59 , pp. 51-55
    • Takasu, K.1    Maiti, S.2    Ihara, M.3
  • 53
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    • For recent representative examples on the cyclization of alkenylurea, see: a
    • For recent representative examples on the cyclization of alkenylurea, see: (a) Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586-14587.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 14586-14587
    • Streuff, J.1    Hövelmann, C.H.2    Nieger, M.3    Muñiz, K.4
  • 61
    • 73149094823 scopus 로고    scopus 로고
    • 2: 24% yield, 12% ee; MeCN: 40% yield, 29% ee; THF: 34% yield, 47% ee; EtOH: 64% yield, 65% ee. See the Supporting Information.
    • 2: 24% yield, 12% ee; MeCN: 40% yield, 29% ee; THF: 34% yield, 47% ee; EtOH: 64% yield, 65% ee. See the Supporting Information.
  • 62
    • 73149105386 scopus 로고    scopus 로고
    • 2 and 22 mol % of (M,S,S)- 3d showed better result. A 61% yield of 2a was obtained with 54% ee when the reaction was conducted at -20°C for 7.1 days as reported in ref 8.
    • 2 and 22 mol % of (M,S,S)- 3d showed better result. A 61% yield of 2a was obtained with 54% ee when the reaction was conducted at -20°C for 7.1 days as reported in ref 8.
  • 64
    • 73149092411 scopus 로고    scopus 로고
    • Abbreviations: (R)-BINAP, R)-2,2′- bis(diphenylphosphino)-1,1′-binaphthyl; (S,S)-t-Bu-BOX, 2,2-bis[(4S)-4-tert-butyl-2-oxazolin-2-yl]propane; (S,S)-i-Pr-BOXAX, S)-2,2′-bis[(4S)-4- isopropyl-2-oxazolin-2-yl]-1,1′-binaphthyl
    • Abbreviations: (R)-BINAP = (R)-2,2′- bis(diphenylphosphino)-1,1′-binaphthyl; (S,S)-t-Bu-BOX = 2,2-bis[(4S)-4-tert-butyl-2-oxazolin-2-yl]propane; (S,S)-i-Pr-BOXAX = (S)-2,2′-bis[(4S)-4- isopropyl-2-oxazolin-2-yl]-1,1′-binaphthyl.
  • 68
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    • For recent representative examples on the cyclization of alkenyl sulfamide, see: a
    • For recent representative examples on the cyclization of alkenyl sulfamide, see: (a) Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250-11251.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 11250-11251
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  • 72
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    • and references cited therein
    • (e) Chemler, S. R. Org. Biomol. Chem. 2009, 7, 3009-3019 and references cited therein.
    • (2009) Org. Biomol. Chem , vol.7 , pp. 3009-3019
    • Chemler, S.R.1
  • 73
    • 0037016260 scopus 로고    scopus 로고
    • For recent representative examples on the cyclization of alkenyl tosylamide, see: a
    • For recent representative examples on the cyclization of alkenyl tosylamide, see: (a) Fix, S. R.; Brice, J. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2002, 41, 164-166.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 164-166
    • Fix, S.R.1    Brice, J.L.2    Stahl, S.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.