Synthesis of a functionalized allylic phosphine oxide

Synthetic Communications

Volumn 27, Issue 17, 1997, Pages 3027-3033

  Harmata, Michael ^a   Carter, Kevin W ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALLYL COMPOUND; PHOSPHINE OXIDE DERIVATIVE;

ARTICLE; BROMINATION; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030842061     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708005007     Document Type: Article

References (22)

1. For reviews of 4+3 cycloadditions, see: (a) Hosomi, A. and Tominaga, Y. (1991) [4+3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I. Eds., Pergamon: Oxford, Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1973, 12, 819.
2. For reviews of 4+3 cycloadditions, see: (a) Hosomi, A. and Tominaga, Y. (1991) [4+3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I. Eds., Pergamon: Oxford, Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1973, 12, 819.
3. For reviews of 4+3 cycloadditions, see: (a) Hosomi, A. and Tominaga, Y. (1991) [4+3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I. Eds., Pergamon: Oxford, Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1973, 12, 819.
4. For reviews of 4+3 cycloadditions, see: (a) Hosomi, A. and Tominaga, Y. (1991) [4+3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I. Eds., Pergamon: Oxford, Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1973, 12, 819.
5. For reviews of 4+3 cycloadditions, see: (a) Hosomi, A. and Tominaga, Y. (1991) [4+3] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I. Eds., Pergamon: Oxford, Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1984, 23, 1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Hoffman, H.M.R. Angew. Chem. Intl. Ed. Engl. 1973, 12, 819.
6. For a review of intramolecular 4+3 cycloadditions, see: Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1997, Vol. 4, (in press).
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15. Our attempts to use allylic phosphines oxides to prepare dienes such as 1 typically result in E/Z mixtures which are inseparable.
16. Alcohol 6 was prepared by DIBAL reduction of the acetal derived from 2-methylene-1,3-propanediol and benzaldehyde. See: (a) Mooradina, A.; Cloke, J.B. J. Am. Chem. Soc. 1945, 67, 942. (b) Wuest, J.D.; Ducharme, Y.; Latour, S. Organometallics 1984, 3, 208.
17. Alcohol 6 was prepared by DIBAL reduction of the acetal derived from 2-methylene-1,3-propanediol and benzaldehyde. See: (a) Mooradina, A.; Cloke, J.B. J. Am. Chem. Soc. 1945, 67, 942. (b) Wuest, J.D.; Ducharme, Y.; Latour, S. Organometallics 1984, 3, 208.
18. 4Pd, THF, 35 °C 24 h, reflux, 24 h.
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