Synlett 2002(11): 1787-1790
DOI: 10.1055/s-2002-34899
LETTER
© Georg Thieme Verlag Stuttgart · New York

New Allylphosphonates Derived from (OCH2CMe2CH2O)PCl and Baylis-Hillman Adducts - Stereochemistry and Utility

C. Muthiaha, K. Senthil Kumara, J. J. Vittalb, K. C. Kumara Swamy*a
a School of Chemistry, University of Hyderabad, Hyderabad- 500046, A. P., India
Fax: +91(40)3012460; e-Mail: kckssc@uohyd.ernet.in;
b Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543 Singapore
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Publication History

Received 2 September 2002
Publication Date:
21 October 2002 (online)

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Abstract

New allylphosphonates have been prepared; an X-ray structural proof for the major Z-isomer has been given for phosphonate 3. Horner-Wadsworth-Emmons reaction of 3 or 6 (Z isomer) with aromatic aldehydes leads to carbomethoxy/ cyano substituted butadienes. In the reaction using cyanoallylphosphonate 6, use of either Z or E isomer leads to the same E,Z product; stereochemistry of one such cyano product is confirmed by X-ray crystallography. In the reaction of 3 with 4-nitrobenzaldehyde stereochemistry for the (E,E) isomer is confirmed by X-ray crystallography.