An isothiourea-catalyzed asymmetric formal [4 + 2] cycloaddition of in situ generated azoalkenes with C1 ammonium enolates?

Organic Chemistry Frontiers Pub Date: 2018-07-30 DOI: 10.1039/C8QO00657A

Abstract

An efficient isothiourea-catalyzed stereoselective formal [4 + 2] cycloaddition of α-chloro cyclic hydrazones with carboxylic acids has been developed. Under mild conditions, a series of functionalized 4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one derivatives with two consecutive stereocenters were obtained in high yields with excellent diastereo- and enantioselectivities (up to >99% ee).

Graphical abstract: An isothiourea-catalyzed asymmetric formal [4 + 2] cycloaddition of in situ generated azoalkenes with C1 ammonium enolates
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