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Volumn 11, Issue 17, 2009, Pages 3914-3917

LIC-KOR-promoted synthesis of alkoxydienyl amines: An entry to 2,3,4,5-tetrasubstituted pyrroles

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; AMINE; DRUG DERIVATIVE; GLYCINE; IMINE; PALLADIUM; PYRROLE DERIVATIVE;

EID: 69449087638     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9015018     Document Type: Article
Times cited : (21)

References (55)
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    • For a recent example of cascade aminopalladation, see
    • For a recent example of cascade aminopalladation, see: Yip, K.-T.; Zhu, N.-Y.; Yang, D. Org. Lett. 2009, 11, 1911.
    • (2009) Org. Lett. , vol.11 , pp. 1911
    • Yip, K.-T.1    Zhu, N.-Y.2    Yang, D.3
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    • Scheffold, R., Eds.; VCH: Weinheim, Germany
    • (b) Schlosser, M. In Modern Synthetic Methods; Scheffold, R., Eds.; VCH: Weinheim, Germany, 1992; p 227.
    • (1992) Modern Synthetic Methods , pp. 227
    • Schlosser, M.1
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    • (c) Mordini, A. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press, Inc.: Greenwich, CT, 1992; Vol.1, pp 1-45.
    • (1992) Advances in Carbanion Chemistry , vol.1 , pp. 1-45
    • Mordini, A.1
  • 51
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    • For a stereoselective approach to dienylamines starting from enantiomerically enriched stannylated allylamines, see
    • For a stereoselective approach to dienylamines starting from enantiomerically enriched stannylated allylamines, see: Reginato, G.; Gaggini, F.; Mordini, A.; Valacchi, M. Tetrahedron 2005, 61, 6791.
    • (2005) Tetrahedron , vol.61 , pp. 6791
    • Reginato, G.1    Gaggini, F.2    Mordini, A.3    Valacchi, M.4
  • 52
    • 69449106117 scopus 로고    scopus 로고
    • N-Boc-dienylamine 2g has been recovered with an unsatisfactory yield (25%, entry 7, Table 1) along with byproducts coming from the damage of the Boc protecting group, which turns out to be unstable under superbasic conditions. N-Protected alkyl imines have not been considered for this work, as they enolize in the superbasic medium.
    • N-Boc-dienylamine 2g has been recovered with an unsatisfactory yield (25%, entry 7, Table 1) along with byproducts coming from the damage of the Boc protecting group, which turns out to be unstable under superbasic conditions. N-Protected alkyl imines have not been considered for this work, as they enolize in the superbasic medium.
  • 53
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    • Enantioselective α-arylglycine synthesis is currently under investigation in our laboratory.
    • Enantioselective (α-arylglycine synthesis is currently under investigation in our laboratory.
  • 54
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    • We decided to consider only N-tosyldienylamines on the grounds that less nucleophilic nitrogen atoms are more reactive in aminopalladation reactions. For examples on this subject, see
    • We decided to consider only N-tosyldienylamines on the grounds that less nucleophilic nitrogen atoms are more reactive in aminopalladation reactions. For examples on this subject, see: Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
    • (2007) Chem. Rev. , vol.107 , pp. 5318
    • Beccalli, E.M.1    Broggini, G.2    Martinelli, M.3    Sottocornola, S.4
  • 55
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    • Attempts to reduce the amount of Pd(II) by the presence of Cu(II) salts as cocatalysts led to low yield of pyrroles.
    • Attempts to reduce the amount of Pd(II) by the presence of Cu(II) salts as cocatalysts led to low yield of pyrroles.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.