Versatile method for the synthesis of 4-substituted 6-methyl-3-oxabicyclo[3.3.1]non-6-ene-1-methanol derivatives: Prins-type cyclization reaction catalyzed by hafnium triflate

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• 作者：Masayuki Nakamura ; Kenji Niiyama ; Takeru Yamakawa
• 关键词：Prins-type cyclization reaction ; Hafnium triflate ; Catalytic reaction ; Oxabicyclo[3.3.1]nonene
• 刊名：Tetrahedron Letters
• 出版年：2009
• 出版时间：25 November 2009
• 年：2009
• 卷：50
• 期：47
• 页码：6462-6465
• 全文大小：1552 K

文摘

A versatile method for the synthesis of 4-substituted 6-methyl-3-oxabicyclo[3.3.1]non-6-ene-1-methanol derivatives has been developed using Prins-type cyclization reaction between aldehydes and O-protected/unprotected cyclohex-3-ene-1,1-dimethanol. Under optimized reaction conditions using hafnium triflate, various substrates, including functionalized benzaldehydes and heteroaromatic carbaldehydes, afforded cyclization products in high yields.