Convenient Preparation of Dimethyl [(3S)‐3‐Methyl‐2‐oxo‐5‐octynyl]‐phosphonate
- 13 November 1989
- journal article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1989 (11) , 1081-1083
- https://doi.org/10.1002/jlac.198919890272
Abstract
The diastereoselective alkylation of the chiral Evans intermediate2with 1‐iodo‐2‐pentyne (3) gives the oxazolidinone4. Titanium alkoxide‐catalysed cleavage yields the ethyl ester5, which is used to acylate dimethyl methanephosphonate to the chiral phosphonate6. The optical purity of phosphonate6is checked by separation on a chiral HPLC column and by conversion into the bromo ketone8, an intermediate for the prostacyclin analogue ZK 96480.Keywords
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