Novel carbonyl-dependent regioselective allylation via diethylzinc- mediated umpolung of π-allylpalladium

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6903-6906

  Kimura, Masanari ^a   Ogawa, Yoshimi ^a   Shimizu, Masamichi ^a   Sueishi, Masayuki ^a   Tanaka, Shuji ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; ACETONE; ALLYL COMPOUND; BENZALDEHYDE; CARBONYL DERIVATIVE; PALLADIUM; TETRAHYDROFURAN; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHELATION; CHEMICAL REACTION; MOLECULAR STABILITY; STEREOCHEMISTRY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0032541719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01448-8     Document Type: Article

References (9)

1. 1) Yasui, K.; Goto, Y.; Yajima, T.; Taniseki, Y.; Fugami, K.; Tanaka, A.; Tamaru, Y. Tetrahedron Lett. 1993, 34, 7619-7622.
2. 2) Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 787-789.
3. 3) Shimizu, M.; Kimura, M.; Tanaka, S.; Tamaru, Y. Tetrahedron Lett. 1998, 39, 609-612.
4. 4) Review: Tamaru, Y. J. Syn. Org. Chem. Jpn. 1995, 53, 1102-1113.
5. 5) van der Schaaf, P. A.; Sutter, J.-P.; Grellier, M.; van Mier, G. P. M.; Spek, A. L.; van Koten, G.; Pfeffer, M. J. Am. Chem. Soc. 1994, 116, 5134-5144.
6. 6) Krämer, T.; Hoppe, D. Tetrahedron Lett. 1987, 28, 5149-5152. Hoppe, D.; Krämer, T. Angew. Chem. 1986, 98, 171-173 and references cited therein.
7. 6) Krämer, T.; Hoppe, D. Tetrahedron Lett. 1987, 28, 5149-5152. Hoppe, D.; Krämer, T. Angew. Chem. 1986, 98, 171-173 and references cited therein.
8. 4) and filtered and the solvents were removed in vacuo. The residue was purified by column chromatography over silica gel to provide spectroscopically homogeneous 5a, 6a, and 7 in 78, 12, and 5% yields, respectively.
9. 8) Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry, 4th ed., Macmillan, New York, 1992, Appendix IV.