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Volumn 7, Issue 1, 2005, Pages 99-108

Addition of benzylic and allylic organozinc and grignard reagents to resin-bound imines to provide α-branched secondary amines bearing a wide variety of functional groups. Utility in the synthesis of β-3 adrenergic receptor agonists

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; BENZYL DERIVATIVE; BETA 3 ADRENERGIC RECEPTOR STIMULATING AGENT; ORGANOMETALLIC COMPOUND; RESIN;

EID: 13544251631     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0498682     Document Type: Article
Times cited : (9)

References (37)
  • 4
    • 13544257257 scopus 로고    scopus 로고
    • 2-Hydroxy-3-(4-hydroxy-3-sulfonamidophenyl)propylamines Useful as Beta 3 Adrenergic Agonists. U.S. Patent 6436914, 8/20/2002
    • (d) Sher, P. M.; Washburn, W. N.; Godfrey, J. 2-Hydroxy-3-(4-hydroxy-3- sulfonamidophenyl)propylamines Useful as Beta 3 Adrenergic Agonists. U.S. Patent 6436914, 8/20/2002.
    • Sher, P.M.1    Washburn, W.N.2    Godfrey, J.3
  • 10
    • 0038106171 scopus 로고    scopus 로고
    • (c) Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 16
    • 13544265446 scopus 로고    scopus 로고
    • Addition to Carbon-Hetero Multiple Bonds
    • Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH GmbH & Co. KGaA: Weinheim, Germany
    • (f) Grosche, P.; Rademann, J.; Jung, G. Addition to Carbon-Hetero Multiple Bonds. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH GmbH & Co. KGaA: Weinheim, Germany, 2002; Vol. 1, pp 322-345.
    • (2002) Handbook of Combinatorial Chemistry , vol.1 , pp. 322-345
    • Grosche, P.1    Rademann, J.2    Jung, G.3
  • 20
    • 0000500365 scopus 로고    scopus 로고
    • (b) For radical mediated diethylzinc addition to an ester-activated oxime ether, see: Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443-1445.
    • (2000) Org. Lett. , vol.2 , pp. 1443-1445
    • Miyabe, H.1    Konishi, C.2    Naito, T.3
  • 22
    • 33751499264 scopus 로고
    • Grignard reagents used were commercially available as either THF or ether solutions, or in most cases, were prepared in ether using "dry- stirred" magnesium according to Baker, K. V.; Brown, J. M.; Hughes, N.; Skarnulis, A. J.; Sexton, A. J. Org. Chem. 1991, 56, 698-703.
    • (1991) J. Org. Chem. , vol.56 , pp. 698-703
    • Baker, K.V.1    Brown, J.M.2    Hughes, N.3    Skarnulis, A.J.4    Sexton, A.5
  • 24
    • 13544259713 scopus 로고    scopus 로고
    • note
    • Small scale separation of diastereomers could be accomplished in about half of the cases attempted by preparative HPLC using a porous graphite Hypercarb column. See Experimental Section, Separation of Diastereomers 3x.
  • 26
    • 13544255552 scopus 로고    scopus 로고
    • note
    • 11 not only deprotonated the methyl group in THF at room temperature, as shown by deuterium quenching, but also added to the imine and cleaved the difluoromethoxy group to generate a phenol.
  • 28
    • 13544269391 scopus 로고    scopus 로고
    • note
    • 1a,c As described herein, similar ratios were produced in reactions of similar resin-bound imines with benzylic Grignard reagents.
  • 29
    • 13544265447 scopus 로고    scopus 로고
    • note
    • 1a,c,d See also Separation of Diastereomers 3x in the Experimental Section.
  • 32
    • 13544273962 scopus 로고    scopus 로고
    • U.S. Patent 3914318
    • 2 in a mixture of 30% aqueous KOH, 2-propanol, and tetrabutylammonium bromide at 80°C; see also U.S. Patent 4316989.
  • 33
    • 13544250615 scopus 로고    scopus 로고
    • U.S. Patent 4316989
    • 2 in a mixture of 30% aqueous KOH, 2-propanol, and tetrabutylammonium bromide at 80°C; see also U.S. Patent 4316989.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.