Unusual Course of the Reaction of Allyl Phosphine Oxides with the Grundmann Ketone

REFERENCES

• Wittig , G. ; Schollkopf , U. Uber triphenyl phosphin methylene als olefinbildende reagenzien . Chem. Ber. 1954 , 87 , 1318 – 1330 .
   Google Scholar
• Maryanoff , B. E. ; Reitz , A. B. The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions: Stereochemistry, mechanism, and selected synthetic aspects . Chem. Rev. 1989 , 89 , 863 – 927 .
   Web of Science ®Google Scholar
• Vedejs , E. ; Peterson , M. J. Stereochemistry and mechanism in the Wittig reaction . Top. Stereochem. 1994 , 21 , 1 – 157 .
   Google Scholar
• Hoffmann , R. W. Wittig and his accomplishments: Still relevant beyond his 100th birthday . Angew. Chem. Int. Ed. 2001 , 40 , 1411 – 1416 .
   PubMed Web of Science ®Google Scholar
• Horner , L. ; Hoffmann , H. ; Wippel , H. G. Phosphorus organic compounds, XII: Phosphine oxides as reagents for olefin formation . Chem. Ber. 1958 , 91 , 61 – 63 .
   Google Scholar
• Horner , L. ; Klink , W. ; Hoffmann , H. Phosphororganische verbindungen, XXXVI: beitrag zur frage der abgrenzung der PO-aktivierten olefinierung von der olefinierung über ylene nach Wittig . Chem. Ber. 1963 , 96 , 3133 – 3140 .
   Google Scholar
• Buss , A. D. ; Warren , S. The stereocontrolled Horner–Wittig reaction: Synthesis of disubstituted alkenes . J. Chem. Soc., Perkin Trans. 1 1985 , 2307 – 2325 .
   Google Scholar
• Lythgoe , B. ; Moran , T. A. ; Nambudiry , M. E. N. ; Ruston , S. ; Tideswell , J. ; Wright , P. W. Allylic phosphine oxides as precursors of dienes of defined geometry: Synthesis of 3-deoxyvitamin D2 . Tetrahedron Lett. 1975 , 3863 – 3866 .
   Google Scholar
• Lythgoe , B. ; Moran , T. A. ; Nambudiry , M. E. N. ; Ruston , S. Allylic phosphine oxides as precursors of conjugated dienes of defined geometry . J. Chem. Soc., Perkin Trans. 1 1976 , 2386 – 2390 .
   Google Scholar
• Lythgoe , B. Synthetic approaches to vitamin D and its relatives . Chem. Soc. Rev. 1980 , 9 , 449 – 475 .
   Web of Science ®Google Scholar
• Dai , H. , Posner , G. H. Synthetic approaches to vitamin D . Synthesis 1994 , 1383 – 1398 .
   Google Scholar
• Okamura , W. H. Synthesis of vitamin D (calciferol) . Chem. Rev. 1995 , 95 , 1877 – 1952 .
   Web of Science ®Google Scholar
• Lythgoe , B. ; Moran , T. A. ; Nambudiry , M. E. N. ; Tideswell , J. ; Wright , P. W. Calciferol and its relatives, part 22: A direct total synthesis of vitamin D2 and vitamin D3 . J. Chem. Soc., Perkin Trans. 1 1978 , 590 – 595 .
   Google Scholar
• Baggiolini , E. G. ; Iacobelli , J. A. ; Hennessy , B. M. ; Batcho , A. D. ; Sereno , J. F. ; Uskokovic , M. R. Stereocontrolled total synthesis of 1α,25-dihydroxycholecalciferol and 1α,25-dihydroxyergocalciferol . J. Org. Chem. 1986 , 51 , 3098 – 3108 .
   Web of Science ®Google Scholar
• Perlman , K. L. ; Swenson , R. E. ; Paaren , H. E. ; Schnoes , H. K. ; DeLuca , H. F. Novel synthesis of 19-nor-vitamin D compounds . Tetrahedron Lett. 1991 , 32 , 7663 – 7666 .
   Web of Science ®Google Scholar
• Sicinski , R. R. 2-Alkylidene analogs of 19-nor-1α,25-(OH)2D3: Synthesis and biological activity. Pol. J. Chem. 2006, 80, 573–585.
   Google Scholar
• Sicinski , R. R. ; Perlman , K. L. ; DeLuca , H. F. Synthesis and biological activity of 2-hydroxy and 2-alkoxy analogs of 1α,25-dihydroxy-19-norvitamin D3 . J. Med. Chem. 1994 , 37 , 3730 – 3738 .
   PubMed Web of Science ®Google Scholar
• Arndt , R. R. ; Warren , S. Connective synthesis of allyl alcohols from allyl phosphine oxides . Tetrahedron Lett. 1978 , 19 , 4089 – 4092 .
   Google Scholar
• Brown , P. S. ; McElroy , A. B. ; Warren , S. Transposition of allylic alcohols controlled by the Ph2PO group: Reagents for α-hydroxy-diene synthesis by the Horner–Wittig reaction . Tetrahedron Lett. 1985 , 26 , 249 – 252 .
   Web of Science ®Google Scholar
• Corey , E. J. ; Enders , D. ; Bock , M. G. A simple and highly effective route to α,β-unsaturated aldehydes . Tetrahedron Lett. 1976 , 17 , 7 – 10 .
   Google Scholar
• Aguiar , A. M. ; Irelan , J. R. S. Michael addition of Grignard reagents to alkynyl-1-phosphine sulfides . J. Org. Chem. 1969 , 34 , 4030 – 4031 .
   Web of Science ®Google Scholar
• Anet , F. A. L. The use of remote deuteration for the determination of coupling constants and conformational equilibria in cyclohexane derivatives . J. Am. Chem. Soc. 1962 , 84 , 1053 – 1054 .
   Web of Science ®Google Scholar
• Miyashita , M. ; Grieco , P. A. Organoselenium chemistry: α-Phenylseleno lactones: New general route to the synthesis of fused α-methylene lactones . J. Org. Chem. 1974 , 39 , 120 – 122 .
   Web of Science ®Google Scholar
• Pietrusiewicz , K. M. ; Zablocka , M. Preparation of scalemic P-chiral phosphines and their derivatives . Chem. Rev. 1994 , 94 , 1375 – 1411 .
   Web of Science ®Google Scholar