The BF3.Et2O promoted thiolytic cleavage of the diastereomeric oxazolidines (1'R)-2 and (1'S)-2 has been studied. The thioacetalisations took place with concomitant thioetherification at the carbinol centres, giving rise to the a-sulfenyl dithioacetals (alpha-SDTA's) (S)-3 and (R)-3 respectively. Selective manipulation of the latter compounds was also achieved. Thus, oxidative hydrolysis gave the corresponding alpha-sulfenyl aldehydes which were shown to be enantiopure.
ASYMMETRIC-SYNTHESIS OF ENANTIOPURE ALPHA-SULFENYL DITHIOACETALS AND ALPHA-SULFENYL ALDEHYDES
MANZONI L;
1993
Abstract
The BF3.Et2O promoted thiolytic cleavage of the diastereomeric oxazolidines (1'R)-2 and (1'S)-2 has been studied. The thioacetalisations took place with concomitant thioetherification at the carbinol centres, giving rise to the a-sulfenyl dithioacetals (alpha-SDTA's) (S)-3 and (R)-3 respectively. Selective manipulation of the latter compounds was also achieved. Thus, oxidative hydrolysis gave the corresponding alpha-sulfenyl aldehydes which were shown to be enantiopure.File in questo prodotto:
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