Direct synthesis of alpha-substituted phosphonates

Authors
Kumar, KP Muthiah, C Kumaraswamy, S Swamy, KCK
Citation
Kp. Kumar et al., Direct synthesis of alpha-substituted phosphonates, TETRAHEDR L, 42(18), 2001, pp. 3219-3221
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
18
Year of publication
2001
Pages
3219 - 3221
Database
ISI
SICI code
0040-4039(20010430)42:18<3219:DSOAP>2.0.ZU;2-B
Abstract
The alpha -subutituted phosphonates (OCH2CMe2CH2O)P(O)CH(X)(Ar) [X=Cl, OMe, NMe2 and OSiMe3], useful precursors for Horner-Wadsworth-Emmons reactions, are readily prepared by treating (OCH2CMe2CH2O)PX with an aromatic aldehyd e. In the reaction of (OCH2CMe2CH2O)PCl with furfuraldehyde and cinnamaldeh yde, the 5-chlorofurfurylphosphonate (OCH2CMe2CH2O)P(O)CH2(5-Cl-C4H2O) and the gamma -chlorophosphonate (OCH2CMe2CH2O)P(O)CH=CH-CH(Cl)Ph, respectively , are formed in good yields. (C) 2001 Published by Elsevier Science Ltd.