Terminal olefin cross-metathesis with acrolein acetals

Tetrahedron Letters

Volumn 40, Issue 6, 1999, Pages 1091-1094

  O'Leary, Daniel J ^b   Blackwell, Helen E ^a   Washenfelder, Rebecca A ^b   Miura, Katsukiyo ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

^b POMONA COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ACROLEIN DERIVATIVE; ALDEHYDE; ALKENE;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; DIMERIZATION; HYDROLYSIS; SYNTHESIS;

EID: 0033524682     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02641-0     Document Type: Article

References (25)

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12. 13C NMR, HRMS).
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17. 2 (2.5 ml) and terminal olefin 3 (0.5 mmol, 1 equiv.) are added in succession. Vinyl dioxolane 8 (1.0 mmol, 2 equiv.) is added and the septum is quickly replaced with a condenser connected to a nitrogen bubbler. The flask is immersed in an oil bath and refluxed (bath temperature: 45 °C) for a period of 12 hr or until the reaction is judged complete by TLC.
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21. 21. Certain homoallylic substituents (Br, OMe, OBn) are known to deactivate catalytic cross-metathesis reactions. See Ref. 10 and: Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999.
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25. 24. We thank the National Institutes of Health and Zeneca Pharmaceuticals for funding this research. DJO thanks Pomona College for provision of a Steele junior faculty leave. HEB thanks the ACS Division of Organic Chemistry for a Graduate Fellowship (supported by Pfizer, Inc.). RAW thanks the Caltech SURF Program and the Pomona College Chemistry Department for a summer fellowship.