Exclusively endo-selective lewis acid-vatalyzed hetero diels-alder reactions of (E)-1-phenylsuifonyl-3-alken-2-ones with vinyl ethers
作者： Eiji Wada , Wen Pei , Hiroshi Yasuoka , Uchou Chin , Shuji Kanemasa
DOI: 10.1016/0040-4020(95)00980-9
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摘要: Abstract ( E )-1-Phenylsulfonyl-3-alken-2-ones as new hetero 1,3-dienes undergo smooth hereto Diels-Alder reactions with vinyl ethers in the presence of a catalytic amount Lewis acid such ZnI 2 , Eu(fod) 3 and TiCl i -PrO) . The are absolutely endo -selective producing 2,4- cis -3,4-dihydro-2 H - pyrans excellent yields, configuration at 3-position depending upon stereochemistry starting ethers. Reductive ring opening 3,4-dihydro-2 -pyran cycloadducts Et SiH/TiCl 4 lead to 6-alkoxy-l-phenylsulfonyl-2-hexanones, sulfonyl-stabilized carbanions derived from 3,4-dthydro-2 alkylated followed by reductive desulfonylation give 2,4,6-trisubstituted derivatives.
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