Asymmetric Organocatalytic Benzylation of Morita–Baylis–Hillman Carbonates with 2,4-Dinitrotoluene Derivatives

Dedicated to Prof. Chi-Wi Ong on the occasion of his retirement

Abstract

The organocatalytic asymmetric benzylation of Morita–Baylis–Hillman (MBH) carbonates with 2,4-dinitrotoluene derivatives as nucleophiles is described. The developed reaction provides a straightforward access to functionalized 2,4-dinitrotoluene derivatives of biological and synthetic relevance. Highly functionalized products have been chemoselectively and efficiently obtained in good to high yields (up to 84%) and with excellent stereoselectivity (up to >20:1 dr, >99 ee).

Key words

asymmetric catalysis - benzylation - MBH carbonates - 2,4-dinitrotoluenes - azaarenes

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