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ChemInform Abstract: Stereoselective Synthesis of a Bicyclic Ketooxetane via a Thionium Ion- Mediated Cyclization Reaction.

✍ Scribed by D. CRAIG; R. M. LAWRENCE; D. J. TAPOLCZAY


Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis


Stereoselective Synthesis of a Bicyclic Ketooxetane via a Thionium Ion-Mediated Cyclization Reaction.

-Et-AlCl2-mediated cyclization of the Z-silyl enol ether onto the thionium ion trigger attached to the five-membered carbocyclic ring gives a good yield the desired bicyclic oxetane (II). It can be easily desulfurized with concomitant carbonyl reduction to the compound (III). Attempted cyclization of the six-membered substrate (IV) produces mainly products of a 1,2-hydride shift. -(CRAIG, D.; LAWRENCE,


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