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Volumn 12, Issue 12, 2010, Pages 2734-2737

Directed lithiation of N -benzenesulfonyl-3-bromopyrrole. Electrophile-controlled regioselective functionalization via dynamic equilibrium between C-2 and C-5 lithio species

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EID: 77953604098     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100810c     Document Type: Article
Times cited : (28)

References (36)
  • 1
    • 77953596613 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 20
    • 77953569553 scopus 로고    scopus 로고
    • Ortho -directing effect of bromine has been reported, see
    • Ortho -directing effect of bromine has been reported, see
  • 24
    • 77953602404 scopus 로고    scopus 로고
    • a values of LTMP, LDA, and LHMDS are 37.3, 35.7, and 29.5, respectively. See: ref 1c
    • a values of LTMP, LDA, and LHMDS are 37.3, 35.7, and 29.5, respectively. See: ref 1c.
  • 26
    • 77953560614 scopus 로고    scopus 로고
    • note
    • LTMP was precipitated as white crystalline solid at -78 °C. This might be the reason for inefficient lithiation of 1 with LTMP in toluene.
  • 27
    • 77953598227 scopus 로고    scopus 로고
    • note
    • 3 complex and related compounds. See
  • 30
    • 77953581556 scopus 로고    scopus 로고
    • note
    • Compound 6 was readily prepared in two steps from N - benzenesulfonylpyrrole. See Supporting Information. We thank Mariko Okamoto for the synthesis of 6.
  • 31
    • 77953554701 scopus 로고    scopus 로고
    • Dynamic equilibrium of organolithiums has been observed in sparteine-mediated enantioselective functionalization of benzylic anions. See ref 1d
    • Dynamic equilibrium of organolithiums has been observed in sparteine-mediated enantioselective functionalization of benzylic anions. See ref 1d.
  • 32
    • 77953599181 scopus 로고    scopus 로고
    • For regioselective syntheses of 2,3- and 2,4-disubstituted pyrroles, see
    • For regioselective syntheses of 2,3- and 2,4-disubstituted pyrroles, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.