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Volumn , Issue 18, 2006, Pages 3110-3114

Palladium(II)-catalyzed synthesis of 2-alkoxytetrahydrofurans from allylic alcohols and vinyl ethers: Stereospecificity and catalysis

Author keywords

Heterocycles; Oxidation; Oxypalladation; Palladium; Palladium hydride elimination

Indexed keywords

2 BUTOXY 4 EXOMETHYLENETETRAHYDROFURAN; 4 BENZYLIDENE 2 ETHOXYTETRAHYDROFURAN; ALCOHOL; ALLYL COMPOUND; COPPER DERIVATIVE; ESTER DERIVATIVE; OXYGEN; PALLADIUM; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 33751262462     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951513     Document Type: Article
Times cited : (13)

References (46)
  • 12
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    • In this report, we use the term of stereospecificity as a classical sense, see: Ward, R. S. Chem. Br. 1991, 803.
    • (1991) Chem. Br. , pp. 803
    • Ward, R.S.1
  • 19
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    • note
    • 3): δ = 1.20 (t, J = 7.2 Hz, 3 H), 2.84 (d, J = 16.8 Hz, 1 H), 2.91-2.98 (dm, 1 H), 3.50 (dq, J = 7.2 Hz, 1 H), 3.78 (dq, J = 7.2 Hz, 1 H), 4.54 (d, J = 12.8 Hz, 1 H), 4.63 (d, J = 12.8 Hz, 1 H), 5.36 (d, J = 5.2 Hz, 1 H), 6.38 (s, 1 H), 7.18-7.36 (m, 5 H).
  • 20
    • 33751291174 scopus 로고    scopus 로고
    • note
    • NOE correlation of vinyl proton (δ = 6.42 ppm) in (Z)-4 was observed with one of C-3 protons (δ = 2.70 ppm), suggesting that these protons are proximal to each other, but not with C-5 protons. On the other hand, vinyl proton (δ = 6.38 ppm) in (E)-5 correlates with one of C-5 protons (δ = 4.54 ppm), but not with C-3 protons (Figure 3). (Diagram presented)
  • 24
    • 0001467798 scopus 로고    scopus 로고
    • As for the chemistry of Pd-H, see: Grushin, V. V. Chem. Rev. 1996, 96, 2011.
    • (1996) Chem. Rev. , vol.96 , pp. 2011
    • Grushin, V.V.1
  • 29
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    • Ref. 5e.
    • Ref. 5e.
  • 33
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    • note
    • 2 (balloon) at r.t. gave quinone 10 in ca. 98% yield (GC). For the survey of these points, the use of catechol itself, instead of 11, was not successful, because the analysis of o-quinone was difficult because of its instability.
  • 35
    • 4544248275 scopus 로고    scopus 로고
    • See also
    • (b) See also: Steinhoff, B. A.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 11268. Although such a catalysis is not necessarily ruled out in the present case, it seems to be difficult to accommodate the observed effect of catechol or quinone into it.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11268
    • Steinhoff, B.A.1    Guzei, I.A.2    Stahl, S.S.3
  • 39
    • 33751304401 scopus 로고    scopus 로고
    • note
    • 2 (balloon). After the mixture was stirred for 0.5 h at r.t. (aging time of catalyst), ethyl vinyl ether (1442 mg, 20 mmol) was added to the flask, and a solution of (E)-3-phenyl-2-propen-1-ol (670 mg, 5.0 mmol) in MeCN (2.5 mL) was then added. The reaction mixture was stirred for 7 h at r.t. In order to determine GC yield of 4, tetraethylene glycol dimethyl ether (63.43 mg) was added to the flask as an internal standard. The GC analysis showed that 82% yield of 4 was formed. This mixture was subjected to purification on a Florisil column (3 g, 10 mm × 80 mm) with elution of EtOAc-n-hexane (1:20, 100 mL), and evaporation of solvent gave 4 (990 mg, 78%) as nearly pure state. (17) Isolation of 2-ethoxy-4-exomethylenetetrahydrofuran derived from 3a was rather difficult because of its lower boiling point, and thus butyl vinyl ether (3b) was used in these experiments.
  • 44
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    • As for Heck reaction, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
    • (1979) Acc. Chem. Res. , vol.12 , pp. 146
    • Heck, R.F.1
  • 46
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    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford
    • (c) Heck, R. F. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 833.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 833
    • Heck, R.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.