催化邻羟基苯基取代对亚甲基醌与酮亚胺环加成反应合成二氢-1,3-苯并噁嗪化合物  

Synthesis of Dihydro-1,3-benzoxazine Compounds via Catalytic Cycloaddition of ortho-Hydroxyphenyl-substituted para-Quinone Methides and Ketimines

作　　者：孙一丹 李鑫 SUN Yidan;LI Xin(College of Chemistry,Nankai University,Tianjin 300071,China;Haihe Laboratory of Sustainable Chemical Transformations,Tianjin 300192,China)

机构地区：[1]南开大学化学学院,天津300071 [2]物质绿色创造与制造海河实验室,天津300192

出　　处：《高等学校化学学报》2024年第2期35-53,共19页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:22371219)资助.

摘　　要：发展了邻羟基苯基取代对亚甲基醌与酮亚胺在磷酸催化体系中的[4+2]环加成反应,以高产率和优良的非对映选择性得到了一系列二氢-1,3-苯并噁嗪化合物.当向反应体系加入催化量的B(C_(6)F_(5))_(3)时,产物的产率得到保持且发生非对映选择性翻转.The[4+2]cycloaddition reaction between ortho-hydroxyphenyl-substituted para-quinone methides and ketimines was carried out in a phosphoric acid catalytic system.A wide range of dihydro-1,3-benzoxazine derivatives were obtained with good yields and excellent diastereoselectivities.When the catalytic amount of B(C_(6)F_(5))_(3) was added to the reaction system,the yield of the product was maintained and the diastereoselectivity was flipped.

关 键 词：邻羟基苯基取代对亚甲基醌 酮亚胺 [4+2]环加成反应 二氢-1 3-苯并噁嗪化合物 非对映选择性翻转 

分 类 号：O626.25[理学—有机化学]