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PANGAEA Supplementary Data
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doi:10.1016/S0040-4039(00)83991-X    
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Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.

Stereochemically controlled synthesis of unsaturated hydroxy-acids by the horner-wittig reaction

Nicholas Greeves and Stuart Warren, *

University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW UK


Received 5 November 1985. 
Available online 8 March 2001.

Abstract

α-Ph2PO-Ketones containing OH and CO2R groups are stereoselectively reduced by NaBH4 under CeC3 catalysis to give Horner-Wittig intermediates for the synthesis of Image -isomers of unsaturated hydroxy-acids.

References

A.D. Buss, N. Greeves, D. Levin, P. Wallace and S. Warren Tetrahedron Lett. 25 (1984), p. 357. Abstract | PDF (207 K) | View Record in Scopus | Cited By in Scopus (1)

P.S. Brown, A.B. McElroy and S. Warren Tetrahedron Lett. 26 (1985), p. 249. Abstract | PDF (220 K) | View Record in Scopus | Cited By in Scopus (5)

P. Wallace and S. Warren Tetrahedron Lett. 26 (1985), p. 5713. Abstract | PDF (168 K) | View Record in Scopus | Cited By in Scopus (4)

D. Levin and S. Warren Tetrahedron Lett. 26 (1985), p. 505. Abstract | PDF (222 K) | View Record in Scopus | Cited By in Scopus (2)

R. Zamboni and J. Rokach Tetrahedron Lett. 24 (1983), p. 999. Abstract | PDF (194 K)
B.J. Fitzsimmons and J. Rokach Tetrahedron Lett. 25 (1984), p. 3043. Abstract | PDF (214 K) | View Record in Scopus | Cited By in Scopus (2)

E.J. Corey and W. Su Tetrahedron Lett. 25 (1984), p. 5119. Abstract | PDF (228 K) | View Record in Scopus | Cited By in Scopus (4)

E.J. Corey, K. Kyler and N. Raju Tetrahedron Lett. 25 (1984), p. 5115. Abstract | PDF (225 K) | View Record in Scopus | Cited By in Scopus (7)

Compounds (17) derived from (5) with an extra chiral centre have a marked tendency to form cyclised products such as the enol ether (18) and the spiro ketal-lactone (16), and will be described in the full paper.

A.L. Gemal and J.-L. Luche J. Am. Chem. Soc. 103 (1981), p. 5454. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (477)

A.B. Smith, B.H. Toder, R.E. Richmond and S.J. Branca J. Am. Chem. Soc. 106 (1984), p. 4001 and references therein . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (5)

For related effects on ketones having an α-dibenzophosphole-5-oxide group

see J. Elliott, S. Warren, submitted to Tetrahedron Lett.


Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 259-262
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