Catalytic asymmetric cycloaddition of unsymmetrical EWG-activated alkenes to fully substituted pyrrolidines bearing three different carbonyl groups.

Chem Commun (Camb)

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. China.

Published: November 2019

A unique 1,3-dipolar [3+2] cycloaddition of alkyl 4-oxo-4-arylbut-2-enoates bearing two different electron-withdrawing groups was completed by using the silver/(R)-DTBM-Segphos catalyst system, which gives the corresponding fully substituted pyrrolidines with four stereogenic centers in good yields and with excellent enantioselectivities (up to 98% ee).

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http://dx.doi.org/10.1039/c9cc07738cDOI Listing

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