메뉴 건너뛰기




Volumn 66, Issue 26, 2010, Pages 4710-4718

Ethynyl MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis

Author keywords

Alkynes Sonogashira coupling; Diels Alder; Iterative cross coupling; MIDA boronates; Small molecule synthesis

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ACETYLENE; BORONIC ACID DERIVATIVE; ETHINYL N METHYLIMINODIACETIC ACID; METHYL GROUP; UNCLASSIFIED DRUG;

EID: 77954243594     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.020     Document Type: Article
Times cited : (72)

References (65)
  • 11
    • 77954243498 scopus 로고    scopus 로고
    • A series of very interesting cycloadditions with ethynyl pinacol ester have recently been reported:
    • A series of very interesting cycloadditions with ethynyl pinacol ester have recently been reported:
  • 18
    • 77954241807 scopus 로고    scopus 로고
    • For the synthesis of 1, see: Lee, S.J.; Burke, M.D. 2010, manuscript in preparation.
    • For the synthesis of 1, see: Lee, S.J.; Burke, M.D. 2010, manuscript in preparation.
  • 24
    • 77954243172 scopus 로고    scopus 로고
    • Iminodiacetic acid can be purchased on the kilogram scale for <$5.50/mol (City Chemical, West Haven, CT, USA).
    • Iminodiacetic acid can be purchased on the kilogram scale for <$5.50/mol (City Chemical, West Haven, CT, USA).
  • 26
    • 77954243240 scopus 로고    scopus 로고
    • For iterative functionalizations of ethynyl tributylstannanes and ethynyl trimethyl silanes, see:
    • For iterative functionalizations of ethynyl tributylstannanes and ethynyl trimethyl silanes, see:
  • 38
    • 0003469528 scopus 로고
    • For a report on the reaction of lithium ethoxyethynyltrialkylboronates with electrophilic reagents, see: B.M. Mikhailov Izv. Akad. Nauk SSSR, Ser. Khim. 4 1979 855 861
    • (1979) Izv. Akad. Nauk SSSR, Ser. Khim. , vol.4 , pp. 855-861
    • Mikhailov, B.M.1
  • 46
    • 77954243254 scopus 로고    scopus 로고
    • For previous hydrometalations of alkynylboranes, see:
    • For previous hydrometalations of alkynylboranes, see:
  • 55
    • 77950390992 scopus 로고    scopus 로고
    • For other examples of selective cross-couplings with differentially- ligated bis-borylated building blocks, see: N. Iwadate, and M. Suginome J. Am. Chem. Soc. 132 2010 2548 2549
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2548-2549
    • Iwadate, N.1    Suginome, M.2
  • 59
    • 15944409961 scopus 로고    scopus 로고
    • For a prior study describing the cycloaddition of diene 11 with a series of alkynyl pinacol esters, see: J.E. Moore, M. York, and J.P.A. Harrity Synlett 2005 860 862
    • (2005) Synlett , pp. 860-862
    • Moore, J.E.1    York, M.2    Harrity, J.P.A.3
  • 60
    • 0000067416 scopus 로고
    • For the synthesis of 11, see D.M. White J. Org. Chem. 39 1974 1951 1952
    • (1974) J. Org. Chem. , vol.39 , pp. 1951-1952
    • White, D.M.1
  • 61
    • 77954243306 scopus 로고    scopus 로고
    • Sigma-Aldrich: 1 700,231, 7 729,221, 8 704,873, 9 704,415.
    • Sigma-Aldrich: 1 700,231, 7 729,221, 8 704,873, 9 704,415.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.