✦ LIBER ✦
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
✍ Scribed by Takeshi Isoda; Ryo Akiyama; Hidekazu Oyamada; Shū Kobayashi
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 104 KB
- Volume
- 348
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
Abstract
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.