Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of <i>C</i>,<i>N</i>-Cyclic Azomethine Imines with Allyl Alkyl Ketones
Guipeng Feng,
Guoyang Ma,
Wenyan Chen,
Shaohong Xu,
Kaikai Wang,
Shaoyan Wang
Affiliations
Guipeng Feng
School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, China
Guoyang Ma
School of Pharmacy, Xinxiang University, Xinxiang 453000, China
Wenyan Chen
School of Pharmacy, Xinxiang University, Xinxiang 453000, China
Shaohong Xu
School of Pharmacy, Xinxiang University, Xinxiang 453000, China
Kaikai Wang
School of Pharmacy, Xinxiang University, Xinxiang 453000, China
Shaoyan Wang
School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, China
A [3 + 2] 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.
