1213779-37-3

Upstream product

• 905307-53-1 (2S)-2-hydroxy-N-methoxy-3-methyl-N-methylbutanamide 
• 905307-55-3 (2S)-2-tert-butyldimethylsilyloxy-N-methoxy-3-methyl-N-methylbutanamide 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 100-52-7 benzaldehyde 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 72-18-4 L-valine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 188659-91-8 N-[(S)-2-Hydroxy-3-methylbutanoyl]pyrrolidine 
• 24347-63-5 methyl (S)-2-hydroxy-3-methylbutanoate 

Downstream Products

• 2768-42-5 (R)-3-phenyl-3-hydroxypropionic acid 
• 36567-72-3 (S)-3-hydroxy-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones

In this work, using DFT calculations, we investigated the 1,4 and 1,5 asymmetric induction in boron enolate aldol reactions of α-alkoxy and α,β-bisalkoxy methyl ketones. We evaluated the steric influence of alkyl substituents at the α position and the stereoelectronic influence of the oxygen protecting groups at the α and β positions. Theoretical calculations revealed the origins of the 1,4 asymmetric induction in terms of the nature of the β-substituent. The synergistic effect between the α,β-syn and α,β-anti-bisalkoxy stereocenters was elucidated. In the presence of the β-alkoxy center, the reaction proceeds through the Goodman-Paton 1,5-stereoinduction model, experiencing a minor influence of the α-alkoxy center.

Stereoselective acetate aldol reactions of α-silyloxy ketones

TiCl4-mediated aldol reactions of chiral methyl α-silyloxy ketones with a variety of aldehydes provide the corresponding 1,4-syn aldol adducts with moderate to high stereocontrol. This transformation represents a new approach to substrate-controlled acetate aldol reactions and complements the 1,4-anti asymmetric induction produced by the related α-benzyloxy ketones. This new approach could be useful in the design of more efficient syntheses of natural products.

1,4-syn-Asymmetric induction in the titanium-mediated aldol reactions of chiral methyl α-silyloxy ketones

Good levels of 1,4-syn asymmetric induction are obtained in the TiCl4-mediated aldol reaction of methyl α-silyloxy ketones with achiral aldehydes. Such methodology represents a new approach to the substrate-controlled acetate aldol reaction, which can be useful to design more efficient syntheses of natural products.