Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.
Nicholas Greeves and Stuart Warren, *
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW UK
Received 5 November 1985.
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
-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 |
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P.S. Brown, A.B. McElroy and S. Warren Tetrahedron Lett. 26 (1985), p. 249. Abstract |
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P. Wallace and S. Warren Tetrahedron Lett. 26 (1985), p. 5713. Abstract |
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D. Levin and S. Warren Tetrahedron Lett. 26 (1985), p. 505. Abstract |
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R. Zamboni and J. Rokach Tetrahedron Lett. 24 (1983), p. 999. Abstract |
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B.J. Fitzsimmons and J. Rokach Tetrahedron Lett. 25 (1984), p. 3043. Abstract |
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E.J. Corey and W. Su Tetrahedron Lett. 25 (1984), p. 5119. Abstract |
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E.J. Corey, K. Kyler and N. Raju Tetrahedron Lett. 25 (1984), p. 5115. Abstract |
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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.






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