✍ Scribed by Thorsten Bach; Frank Eilers
No coin nor oath required. For personal study only.
The ring opening of 3-isopropyl-2-phenyl-3-oxetanol (2a) by (42% yield) and 26 (54% yield). Other 2-phenyl-3-oxetanols such as 2b and 2c can also be employed as electrophiles, various nucleophiles has been studied. In the presence of BF 3 as a Lewis acid, a clean reaction at the less substituted C-4 whereas 2-anisyl derivatives preferentially undergo rearrangement reactions, as exemplified by the conversion of position was observed and the corresponding 1,2-diols 6-11 and 21-23 were isolated in diastereomerically pure form (47-oxetane 16 to the hydroxy ketone 17 (84% yield). The superior behaviour of 3-oxetanols as compared to their silyl 97% yield). Alkyl-, aryl-, alkynyl-and alkenyllithium compounds proved to be suitable carbon nucleophiles. derivatives in reactions with nucleophiles became evident from the reaction of 3-silyloxyoxetane 1a with alkyllithium Deprotonated thiols were used as sulfur nucleophiles. An alkoxide derived from benzyl alcohol and an amide derived reagents. A β elimination occurred upon treatment with nBuLi, which, after pericyclic ring opening and addition of from benzylamine reacted less readily under these conditions, yielding the 1,2,3-trifunctional compounds 24 nBuLi, yielded the allylic alcohol 20.
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