A 100 Gram‐Scale Production of a Key Building Block of Antibacterial Vancomycin: The Use of an Air‐Stable Chiral Zirconium Catalyst and Complete Recovery of a Silicon Source in Catalytic Asymmetric Mukaiyama Aldol Reaction

We have achieved a 100 gram‐scale production of anti ‐(2 S ,3 S )‐β‐( p ‐benzyloxy‐ m ‐chloro)phenyl‐ N ‐trifluoroacetyl‐ L ‐serine methyl ester ( 1 ) in high yield with high diastereo‐ and enantioselectivities based on a catalytic asymmetric Mukaiyama aldol reaction. The use of an air‐stable zirconium‐molecular sieves combined catalyst [( R )‐I 4 ‐ZrMS] facilitates easy manufacturing operation and reproducibility. Moreover, this is the first example of the complete recovery of the silicon source in a Mukaiyama aldol reaction.