Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 65, Issue 15, Pages 4487-4497Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9918596
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A catalytic enantioselective inverse-electron demand hetero-Diels-Alder reaction of alpha,beta-unsaturated carbonyl compounds with electron-rich alkenes catalyzed by chiral. bisoxazolines in combination with Cu(OTf)(2) as the Lewis acid is presented. The reaction of gamma-substituted beta,gamma-unsaturated alpha-keto esters with vinyl ethers and Various types of cis-disubstituted alkenes proceeds in good yield, high diastereoselectivity, and excellent enantioselectivity. The potential of the reaction is demonstrated by the synthesis of optically active carbohydrates such as spiro-carbohydrates, an ethyl beta-D-mannoside tetraacetate, and acetal-protected C-2-branched carbohydrates. On the basis of X-ray crystallographic data and the absolute configuration of the products, it is proposed that the alkene approaches the si-face of the reacting alpha,beta-unsaturated carbonyl functionality when coordinated to the catalyst.
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