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Novel asymmetric synthesis of a bicyclo[3.1.0]hexane derivative by an efficient retro-diels-alder strategy

โœ Scribed by Eric D. Moher


Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
192 KB
Volume
37
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The first preparation of enantiomerically pure bicyclo[3.1.0]hexane-2-one-6-carboxylic acid ethyl ester (1), a valuable synthetic intermediate, is described. The synthesis features a retro-Diels-Alder reaction as a key step. Conditions which allow for a high yielding thermal conversion of 3 to 4 are described.


๐Ÿ“œ SIMILAR VOLUMES


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The bicyclo[3.2.l]octane ring system is assembled by a three-step process featuring a thermally induced [4+2] cycloaddition followed by a 1,3benzodithiolium ion mediated cyclization onto an enol or silyl enol ether double bond. The bicyclo[3.2.l]octane carbon skeleton is a common structural subunit

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