Copper/Chiral Phosphoric-Acid-Catalyzed Intramolecular Reductive Isocyanide-Alkene (1 + 2) Cycloaddition: Enantioselective Construction of 2-Azabicyclo[3.1.0]hexanes,Journal of the American Chemical Society

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Copper/Chiral Phosphoric-Acid-Catalyzed Intramolecular Reductive Isocyanide-Alkene (1 + 2) Cycloaddition: Enantioselective Construction of 2-Azabicyclo[3.1.0]hexanes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-03-12 , DOI: 10.1021/jacs.4c00989
Sidi Cheng _{1,

2} , Ting Yu _{1,

2} , Jing Li _{1,

2} , Yingxiang Liang _{1,

2} , Shuang Luo _{1,

2} , Qiang Zhu _{1,

2,

3}

Affiliation

Enantioenriched 2-azabicyclo[3.1.0]hexanes are accessed from readily available allyl substituted α-isocyanoesters by intramolecular (1 + 2) cycloaddition with the olefinic moiety and isocyano carbon as the respective C2 and C1 units. Cyclopropanation is initiated by 1,1-hydrocupration of isocyanide followed by formimidoylcopper to copper α-aminocarbenoid equilibration and subsequent (1 + 2) cycloaddition. The unprecedented copper/chiral phosphoric acid (CPA) catalytic system can be operated in the presence of water under air, delivering a variety of 2-azabicyclo[3.1.0]hexanes containing an angular all-carbon quaternary stereocenter in good to excellent yields and enantioselectivity.

中文翻译：

铜/手性磷酸催化的分子内还原异氰化物-烯烃 (1 + 2) 环加成：2-氮杂双环[3.1.0]己烷的对映选择性构建

对映体富集的2-氮杂双环[3.1.0]己烷是通过烯基部分和异氰基碳作为各自的C2和C1单元的分子内(1+2)环加成从容易获得的烯丙基取代的α-异氰酸酯获得的。环丙烷化反应由异氰化物的 1,1-氢化反应引发，随后甲亚胺酰铜与铜 α-氨基类胡萝卜素平衡，随后进行 (1 + 2) 环加成。前所未有的铜/手性磷酸（CPA）催化系统可以在空气中有水的情况下运行，以良好至优异的收率提供各种含有角全碳四元立构中心的2-氮杂双环[3.1.0]己烷。对映选择性。

更新日期：2024-03-12

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