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STEREOCHEMISTRY OF 1,2-OXAPHOSPHOLANES-I SYNTHESIS, 1H AND 13C NMR STUDIES AND EQUILIBRATION OF DIASTEREOMERIC 2-METHOXY-2-OXO-3,5,5-TRIMETHYL-1,2-OXAPHOSPHOLAN-3-OLS
Wroblewski, A. E.
, p. 1809 - 1816 (2007/10/02)
Both diastereomers 1A and 1B of the title compound were obtained for the first time, as well as the ring-opened product 6.Pure 1A and 1B were equilibrated in the presence of sodium methoxide in methanol to give 45:55 mixture of 1A and 1B.The same mixture was produced from 6 with either MeONa/MeOH or HCl/MeOH solutions.Triethylamine-catalyzed cyclisation of 6 led to a 15:85 mixture of 1A and 1B.The cis relationship of the OH and P=O groups in 1A and 7A was established by 1H and 13CNMR spectra.Predominant conformations of 1A and 1B and their derivatives were deduced from 3JHCCP and 3JCCOP coupling constants.A possible mechanism of the transformations described in the paper is discussed.
