双环吡唑烷酮衍生物的非对映选择性催化[3 + 3]-环加成反应烯基重氮乙酸酯与亚胺氮。
Bicyclic pyrazolidinone derivatives from diastereoselective catalytic [3 + 3]-cycloaddition reactions of enoldiazoacetates with azomethine imines.
机构信息
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
出版信息
Org Lett. 2013 Apr 5;15(7):1564-7. doi: 10.1021/ol400339c. Epub 2013 Mar 11.
Abstract
A highly regio- and diastereoselective synthesis of bicyclic pyrazolidinone derivatives by rhodium(II) acetate catalyzed [3 + 3]-annulation with enoldiazoacetates and azomethine imines has been achieved in high yield. A vinylogous reaction of the metal enol carbene with the azomethine imine initiates [3 + 3]-cycloaddition, whereas reaction at the carbene center effects N-N-cleavage of the azomethine imine.
摘要
通过铑（II）醋酸盐催化的烯醇重氮乙酸酯和亚胺腙的[3+3]-环加成反应，高产率地实现了双环吡唑烷酮衍生物的高区域和立体选择性合成。金属烯醇卡宾与亚胺腙的烯丙基反应引发[3+3]-环加成，而卡宾中心的反应则导致亚胺腙的 N-N 键断裂。
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