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Synlett 2001; 2001(4): 0481-0484
DOI: 10.1055/s-2001-12333
DOI: 10.1055/s-2001-12333
letter
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Highly Stereoselective Diels-Alder Reactions Achieved on Some Hexopyranosidic Templates
Further Information
Publication History
Publication Date:
31 December 2001 (online)
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The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.
asymmetric synthesis - diastereoselectivity - Diels-Alder reaction - cyclopentadiene - norbornene derivatives