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| - Facile Chemo-, Regio-, and DiastereoselectiveApproach to cis-3,5-Disubstitutedγ-Butyrolactones and Fused γ-Butyrolactones
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| - Chemoselective SN2‘ condensation of primary enolates ofalkyl methyl ketones 2a−e with dimethyl bromomethylfumarate (1) followed by highly diastereoselective NaBH4reduction of the ketone function in the formed ketodiesters3a−e and the regioselective in situ lactonization of theunisolable intermediates 4a−e exclusively furnished the cis-3,5-disubstituted γ-butyrolactones (±)-5a−e in very goodyields. Similarly, the face-selective coupling reaction ofcyclohexanone enolate with 1 to form a mixture of diastereomers in an 8:2 ratio followed by a highly selectivereductive cyclization of 9 plus 10 exclusively provided thecis-octahydrobenzofuran (±)-12 in 70% overall yield.
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