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Volumn 352, Issue 18, 2010, Pages 3136-3140

Highly diastereoselective indium-mediated allenylation of N-tert-butanesulfinyl imino ester: Efficient synthesis of optically active α-allenylglycines

Author keywords

allenylglycine; allenylation; cis substituted proline; indium; N tert butanesulfinyl imino ester

Indexed keywords


EID: 78650311806     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000688     Document Type: Article
Times cited : (31)

References (71)
  • 1
    • 78650356037 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 10
    • 4544276732 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 1196-1216.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1196-1216
  • 13
    • 22944485617 scopus 로고    scopus 로고
    • S. Ma, Chem. Rev. 2005, 105, 2829-2872
    • (2005) Chem. Rev. , vol.105 , pp. 2829-2872
    • Ma, S.1
  • 16
  • 25
    • 78650312469 scopus 로고    scopus 로고
    • For recent reviews on the chemistry of N-tert-butanesulfinimines, see
    • For recent reviews on the chemistry of N-tert-butanesulfinimines, see
  • 42
    • 78650341626 scopus 로고    scopus 로고
    • It is known that the related organoindium intermediates could form by the reaction of propargyl bromide with indium, for selected examples, see
    • It is known that the related organoindium intermediates could form by the reaction of propargyl bromide with indium, for selected examples, see
  • 47
    • 78650366716 scopus 로고    scopus 로고
    • When simple 3-bromopropyne without R substitution was employed, only the propargylation product was isolated in 16% yield, see Supporting Information
    • When simple 3-bromopropyne without R substitution was employed, only the propargylation product was isolated in 16% yield, see Supporting Information.
  • 48
    • 78650338461 scopus 로고    scopus 로고
    • With aliphatic substrates 2j, 2k and 2l, the propargylation products were isolated in 10%, 8% and 5% yields, respectively
    • With aliphatic substrates 2j, 2k and 2l, the propargylation products were isolated in 10%, 8% and 5% yields, respectively.
  • 49
    • 78650355510 scopus 로고    scopus 로고
    • For selected reviews, see
    • For selected reviews, see
  • 50
    • 51249100498 scopus 로고    scopus 로고
    • A. Arcadi, Chem. Rev. 2008, 108, 3266-3325
    • (2008) Chem. Rev. , vol.108 , pp. 3266-3325
    • Arcadi, A.1
  • 56
    • 78650410286 scopus 로고    scopus 로고
    • Compound 3a was oxidized to 4 by oxone in consideration of avoiding unnecessary metal chelation to the sulfinyl group
    • Compound 3a was oxidized to 4 by oxone in consideration of avoiding unnecessary metal chelation to the sulfinyl group.
  • 57
    • 78650377584 scopus 로고    scopus 로고
    • The cis-configuration was confirmed by the NOE experimentation, and the dr ratio was determined by LC-MS. For products 9 and 10, 96.4:3.6 and 98.6:1.4 isomeric ratios were observed, respectively
    • The cis-configuration was confirmed by the NOE experimentation, and the dr ratio was determined by LC-MS. For products 9 and 10, 96.4:3.6 and 98.6:1.4 isomeric ratios were observed, respectively.
  • 58
    • 78650359839 scopus 로고    scopus 로고
    • For selected examples, see
    • For selected examples, see
  • 65
    • 78650407397 scopus 로고    scopus 로고
    • note
    • (int)=0.0278). CCDC 791486 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
  • 66
    • 78650375069 scopus 로고    scopus 로고
    • For related crystal structures and theoretical calculations support
    • For related crystal structures and theoretical calculations support


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.