Novel asymmetric synthesis of a bicyclo[3.1.0]hexane derivative by an efficient retro-diels-alder strategy
โ 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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โฆ 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.
๐ SIMILAR VOLUMES
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
AbstractรExocyclic arylidene derivatives have been used as dienophiles in DielsยฑAlder reactions with cyclopentadiene. A series of novel heterocyclic derivatives containing the spiro bicyclo[2.2.1]heptane system is the outcome of such reactions. The reactions proceed with high exoselectivity in the p