Direct α-functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis.

Junming Mo, Ruojie Yang, Xingkuan Chen, Bhoopendra Tiwari, Yonggui Robin Chi

Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

Organic letters 2013 Jan 4

filter terms:

A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.

Citation

Junming Mo, Ruojie Yang, Xingkuan Chen, Bhoopendra Tiwari, Yonggui Robin Chi. Direct α-functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis. Organic letters. 2013 Jan 4;15(1):50-3