Synthesis of a Functionalized Allylic Phosphine Oxide

References

• For reviews of 4+3 cycloadditions, see: (a) Hosomi A. Tominaga Y. [4+3] Cycloadditions Comprehensive Organic Synthesis Trost B. M. Fleming I. Pergamon Oxford 1991 Vol. 5 593 615 Chapter 5.1
   Google Scholar
• Hoffman , H. M.R. 1984 . Angew. Chem. Intl. Ed. Engl. , 23 : 1
   Google Scholar
• Mann , J. 1986 . Tetrahedron , 42 : 4611
   Web of Science ®Google Scholar
• Noyori , R. and Hayakawa , Y. 1983 . Org. React. , 29 : 163 – 344 .
   Web of Science ®Google Scholar
• Hoffman , H. M.R. 1973 . Angew. Chem. Intl. Ed. Engl. , 12 : 819
   Google Scholar
• For a review of intramolecular 4+3 cycloadditions, see: Harmata M. Advances in Cycloaddition Lautens M. JAI Greenwich 1997 Vol. 4 (in press)
   Google Scholar
• Hansson , T. and Wickberg , B. 1992 . J. Org. Chem. , 57 : 5370
   Google Scholar
• Mehta , G. , Krishnamurthy , N. and Rao Karra , S. 1991 . J. Am. Chem. Soc. , 113 : 5765
   Google Scholar
• Mehta , G. 1990 . Pure Appl. Chem. , 61 : 1263
   Google Scholar
• Mehta , G. , Krishnamurthy , N. and Rao Karra , S. 1989 . J. Chem. Soc., Chem. Commun. , : 1299
   Google Scholar
• Shizuri , Y. , Yamaguchi , S. , Terada , Y. and Yamamura , S. 1986 . Tetrahedron Lett. , 27 : 57
   Google Scholar
• Nishizawa , M. , Inoue , A. , Hayashi , Y. , Sastrapradja , S. , Kosela , S. and Iwashita , T. 1984 . J. Org. Chem. , 49 : 3662
   Google Scholar
• Yamamoto , H. , Ukaki , I. , Ikeda , Y. and Ikeda , N. 1983 . Tetrahedron Lett. , 24 : 4029
   Google Scholar
• Shen , Y. and Wang , T. 1991 . Tetrahedron Lett. , 32 : 4353
   Google Scholar
• Our attempts to use allylic phosphines oxides to prepare dienes such as 1 typically result in E/Z mixtures which are inseparable.
   Google Scholar
• Alcohol 6 was prepared by DIBAL reduction of the acetal derived from 2-methylene-1,3-propanediol and benzaldehyde. See: Mooradina A. Cloke J. B. J. Am. Chem. Soc. 1945 67 942
   Google Scholar
• Wuest , J. D. , Ducharme , Y. and Latour , S. 1984 . Organometallics , 3 : 208
   Google Scholar
• Other attempts which failed to give rearrangement product: (1) decalin, 150°C, sealed tube, 24 h; (2) decane, reflux, 24 h; (3) 5 mol % (Ph3P)4Pd, THF, 35 °C 24 h, reflux, 24 h.
   Google Scholar
• Byun , H. S. , Reddy , K. C. and Bittman , R. 1994 . Tetrahedron Lett. , 35 : 1371
   Web of Science ®Google Scholar
• Vilieras , J. and Rambaud , M. 1988 . Org. Synth. , 66 : 220
   Google Scholar
• Tadano , K. , Idogaki , Y. , Yamada , H. and Suami , T. 1987 . J. Org. Chem. , 52 : 1201
   Web of Science ®Google Scholar
• Kann , N. , Rein , T. , Akermark , B. and Helquist , P. 1990 . J. Org. Chem. , 55 : 5312
   Google Scholar