Chelation-controlled regioselection in palladium-catalyzed carbonyl allylation by 4-pentene-1,3-diol or its cyclic carbonate

Synthetic Communications

Volumn 27, Issue 6, 1997, Pages 1015-1021

  Masuyama, Yoshiro ^a   Mochizuki, Susumu ^a   Kurusu, Yasuhiko ^a  

^a SOPHIA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030887480     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708003045     Document Type: Article

References (11)

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3. Yanagisawa, A.; Habaue, S.; Yasue, K. and Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6130.
4. Masuyama, Y.; Hayakawa, A.; Kishida, M. and Kurusu, Y. Inorg. Chim. Acta 1994, 220, 155.
5. Masuyama, Y.; Kishida, M. and Kurusu, Y. J. Chem. Soc., Chem. Commun. 1995, 1405.
6. Takahara, J. P.; Masuyama, Y. and Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577; Masuyama, Y. in "Advances in Metal-Organic Chemistry," Liebeskind, L. S. Ed, JAI Press, London, 1994, Vol. 3, pp. 255-303.
7. Takahara, J. P.; Masuyama, Y. and Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577; Masuyama, Y. in "Advances in Metal-Organic Chemistry," Liebeskind, L. S. Ed, JAI Press, London, 1994, Vol. 3, pp. 255-303.
8. Bando, T.; Tanaka, S.; Fugami, K.; Yoshida, Z. and Tamaru, Y. Bull. Chem. Soc. Jpn. 1992, 65, 97.
9. Tamaru, Y.; Hojo, M.; Kawamura, S.; Sawada, S. and Z. Yoshida, J. Org. Chem. 1987, 52, 4062.
10. 1H NMR (JEOL GX-270) of 2-phenyl-3-vinyltetrahydrofuran (5; R=Ph) suggested that the stereochemistry in a major isomer of all 2-substituted 3-vinyltetrahydrofurans 5 was trans (cis:trans=1:9).
11. Cyclic carbonate of 4-hexene-1,3-diol, namely 4-[(E)-2-propenyl]-1,3-dioxan-2-one caused the carbonyl allylation at room temperature neither in DMF nor in THF.