螺环[4.5]环己二烯酮的设计、合成及应用——一锅法顺序羟苄基化/氧化去芳构化。
Design, synthesis and application of spiro[4.5]cyclohexadienones one-pot sequential -hydroxybenzylation/oxidative dearomatization.
机构信息
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India and Department of Analytical and Structural chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
出版信息
Chem Commun (Camb). 2021 Jun 3;57(45):5574-5577. doi: 10.1039/d1cc01752g.
One-pot sequential p-hydroxybenzylation/oxidative dearomatization/spiroannulation has been designed for the efficient construction of tetrahydrofuran containing spiro-cyclohexadienones. This reaction proceeds through the p-hydroxybenzylation of 1,3-diketones with p-hydroxybenzyl alcohol via quinone methide formation followed by oxidative dearomatization/spiroannulation with suitable alcohols. The Friedel-Crafts alkylation of spiro[4.5]cyclohexadienones with indoles provided a broad array of highly diastereoselective C-3 alkylated spirocycles and cyclohepta[b]indoles depending upon the ring size of the fused cyclic ketones.
一锅法顺序对羟苄基化/氧化去芳构化/螺环化反应被设计用于高效构建含四氢呋喃的螺环环己二烯酮。该反应通过醌甲醚形成，使 1,3-二酮与对羟苄醇进行对羟苄基化，然后与合适的醇进行氧化去芳构化/螺环化。螺[4.5]环己二烯酮与吲哚的傅克烷基化反应提供了一系列广泛的高度非对映选择性 C-3 烷基化螺环和环庚[b]吲哚，具体取决于稠合环状酮的环大小。
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