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Volumn 136, Issue 42, 2014, Pages 14951-14958

Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS; STEREOSPECIFIC; TETRAHYDROFURANS;

EID: 84908440157     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5076426     Document Type: Article
Times cited : (71)

References (95)
  • 8
    • 84908439033 scopus 로고    scopus 로고
    • Biosynthesis of "Unnatural " Natural Products
    • Bartlett, P. A., Entzeroth, M., Eds.; Royal Society of Chemistry: Dorset, U.K.
    • (a) Tang, Y.; Khosla, C. Biosynthesis of "Unnatural " Natural Products. In Exploiting Chemical Diversity for Drug Discovery; Bartlett, P. A., Entzeroth, M., Eds.; Royal Society of Chemistry: Dorset, U.K., 2006.
    • (2006) Exploiting Chemical Diversity for Drug Discovery
    • Tang, Y.1    Khosla, C.2
  • 39
    • 84908439032 scopus 로고    scopus 로고
    • note
    • We have observed that es is typically higher at lower catalyst loadings; this holds true for cross-coupling of THP 7 as well. With 10 mol % catalyst loading affords >99% es; 15 mol % catalyst loading provides 88% es. For a rationale and mechanistic experiments, see ref 12d.
  • 40
    • 84908439031 scopus 로고    scopus 로고
    • note
    • 2 (vide infra, Table 4).
  • 45
    • 84908439030 scopus 로고    scopus 로고
    • Asymmetric Catalysis in the Total Synthesis of Lipids and Polyketides
    • Christmann, M., Brase, S., Eds.; Wiley-VCH: Weinheim, Germany
    • Barroso, S.; Minnaard, A. J. Asymmetric Catalysis in the Total Synthesis of Lipids and Polyketides. In Asymmetric Synthesis: More Methods and Applications; Christmann, M., Brase, S., Eds.; Wiley-VCH: Weinheim, Germany, 2012.
    • (2012) Asymmetric Synthesis: More Methods and Applications
    • Barroso, S.1    Minnaard, A.J.2
  • 54
    • 84908439029 scopus 로고    scopus 로고
    • note
    • The Breit model was used to assign the relative configuration of cis- and trans- 12 see ref 19b. See SI for full details.
  • 61
    • 84908439028 scopus 로고    scopus 로고
    • note
    • See SI for details.
  • 85
    • 84908439027 scopus 로고    scopus 로고
    • note
    • For data with a series of ligands, see the SI Section C.
  • 86
    • 84908439026 scopus 로고    scopus 로고
    • note
    • We have previously established that nickel-catalyzed Negishitype cross-couplings of benzylic esters proceed with inversion at the benzylic C-O bond. We have therefore assigned the absolute configuration of the afforded carboxylic acids as the S-enantiomers. See ref 44.
  • 94
  • 95
    • 84908439025 scopus 로고    scopus 로고
    • note
    • Both enantiomers of lactone 59 are commercially available or can be synthesized in 5 steps from 6-methoxynaphthaldehyde using CBS reduction as a key step. See SI for full details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.