Gold and platinum catalyzed cascade reaction of propargyl acetates bearing terminal alkynes or methyl ketones

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• 作者：Taichi Kusakabe^a ; Keisuke Kato ; ^a ; ^{kkk@toho-u.ac.jp}
• 关键词：Propargyl acetate ; Gold(III) ; Platinium(IV) ; Cycloisomerization ; Acyloxy migration
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：18 February 2011
• 年：2011
• 卷：67
• 期：7
• 页码：1511-1517
• 全文大小：461 K

文摘

A gold (III)-catalyzed cascade reaction of propargyl acetates bearing an extra terminal alkyne (1) afforded γ-keto esters 3 and lactones 4. These products should be generated through allenyl ketone intermediate B via a 1,2-acyloxy cyclization/fragmentation/cycloisomerization/hydrolysis sequence. On the other hand, the cascade reaction of α-acetoxy ketones bearing terminal alkynes 5 afforded lactone 6 via allenyl ketone intermediate A. This reaction involves a [3,3]-sigmatropic acyloxy rearrangement/cycloisomerization/hydrolysis sequence.