Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade.,Chemical Science

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Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade.
Chemical Science ( IF 7.6 ) Pub Date : 2019-07-29 , DOI: 10.1039/c9sc02828e
Marco Brandstätter ₁ , Nikolas Huwyler ₁ , Erick M Carreira ₁

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Stereoselective synthesis of bicyclo[3.3.0]octenones from chiral 1,3-enyne aldehydes bearing propargylic acetates is described. The method is based on a Au(i)-catalyzed domino sequence with concomitant transfer of chirality involving 1,3-acyloxy migration followed by Nazarov cyclization and an unprecedented aldol addition. The method furnishes densely functionalized bicyclic structures in high yields, with up to 97% ee and good diastereoselectivity.

中文翻译：

通过1,3-酰氧基迁移/纳扎罗夫环化/醛醇加成级联反应的金（i）催化的1,3-烯炔醛的立体选择性环化。

描述了由带有炔丙基乙酸酯的手性1，3-烯炔醛立体选择性地合成双环[3.3.0]辛烯酮。该方法基于Au（i）催化的多米诺骨牌序列，伴随手性转移，涉及1,3-酰氧基迁移，然后进行Nazarov环化和前所未有的醛醇加成。该方法可提供高收率的致密功能化双环结构，ee最高可达97％，非对映选择性良好。

更新日期：2019-07-29

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