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Convenient Preparation of Dimethyl [(3S)‐3‐Methyl‐2‐oxo‐5‐octynyl]‐phosphonate
Author(s) -
Harre Michael,
Trabandt Jörg,
Westermann Jürgen
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890272
Subject(s) - phosphonate , chemistry , alkylation , alkoxide , ketone , cleavage (geology) , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
The diastereoselective alkylation of the chiral Evans intermediate 2 with 1‐iodo‐2‐pentyne ( 3 ) gives the oxazolidinone 4 . Titanium alkoxide‐catalysed cleavage yields the ethyl ester 5 , which is used to acylate dimethyl methanephosphonate to the chiral phosphonate 6 . The optical purity of phosphonate 6 is checked by separation on a chiral HPLC column and by conversion into the bromo ketone 8 , an intermediate for the prostacyclin analogue ZK 96480.