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DOI: 10.1055/sos-SD-204-00303

Chiang, P. -C.; Bode, J. W.Science of Synthesis: Asymmetric Organocatalysis, (20121669.

There have been few catalyst types and reaction modalities that have seen such rapid growth and prevalence in such a short period of time as the chemistry of N-heterocyclic carbene catalyzed reactions of α-functionalized aldehydes. Five discrete reactive intermediates are generated from a single starting material: (i) acyl anion equivalents, (ii) homoenolate equivalents; (iii) ester enolate equivalents, (iv) saturated acyl azoliums (activated carboxylates), and (v) α,β-unsaturated acyl azoliums. In each case, chiral catalysts have been identified that allow for highly enantio- and diastereoselective reactions. Given the vast number of useful transformations reported since 2004, it can be expected that this chemistry will continue to see impressive developments and applications in the coming years.