188659-95-2

Upstream product

• 100-44-7 benzyl chloride 
• 188659-91-8 N-[(S)-2-Hydroxy-3-methylbutanoyl]pyrrolidine 
• 63674-18-0 ethyl (2S)-2-hydroxy-3-methylbutanoate 
• 24347-63-5 methyl (S)-2-hydroxy-3-methylbutanoate 

Downstream Products

• 1415121-52-6 (S)-3-benzyloxy-4-methyl-2-pentanone 
• 1415122-09-6 (3S,6S)-3-benzyloxy-6-hydroxy-2,7-dimethyl-4-octanone 
• 1415122-10-9 (3S,6R)-3-benzyloxy-6-hydroxy-2,7-dimethyl-4-octanone 
• 1415122-11-0 (1S,4S)-4-benzyloxy-1-hydroxy-5-methyl-1-phenyl-3-hexanone 
• 1415122-12-1 (1R,4S)-4-benzyloxy-1-hydroxy-5-methyl-1-phenyl-3-hexanone 
• 1415122-13-2 (3S,6S)-3-benzyloxy-6-hydroxy-2,7-dimethyl-7-octen-4-one 
• 1415122-14-3 (3S,6R)-3-benzyloxy-6-hydroxy-2,7-dimethyl-7-octen-4-one 

Relevant academic research and scientific papers

Stereoselective titanium-mediated aldol reactions of α-benzyloxy methyl ketones

Good levels of 1,4-anti asymmetric induction are obtained in the TiCl 3(i-PrO)-mediated aldol reaction of chiral α-benzyloxy methyl ketones with a wide array of aldehydes. This methodology represents a new approach to substrate-controlled acetate aldol reactions capable of providing highly functionalized fragments in a straightforward manner, which may be useful in the design of more efficient syntheses.

Stereoselective titanium-mediated aldol reactions of α-benzyloxy methyl ketones

Good levels of 1,4-anti asymmetric induction are obtained in the TiCl 3(i-PrO)-mediated aldol reaction of chiral α-benzyloxy methyl ketones with a wide array of aldehydes. This methodology represents a new approach to substrate-controlled acetate aldol reactions capable of providing highly functionalized fragments in a straightforward manner, which may be useful in the design of more efficient syntheses.

Simple and efficient preparation of enantiopure alkyl α-hydroxyalkyl ketones

The acylation reaction of organolithium reagents with pyrrolidine-derived α-benzyloxy and α-silyloxy carboxamides provides a simple and high-yielding method for the preparation of enantiopure α-benzyloxy and α-silyloxy ketones.

A simple procedure for the preparation of enantiopure ethyl α-hydroxyalkyl ketones

Amides derived from pyrrolidine and methyl (S)-lactate, methyl (S)-2-hydroxy-3-phenylpropanoate, or methyl (S)-2-hydroxy-3-methylbutanoate, after O-benzylation and O-silylation have been treated with EtLi or EtMgCl under suitable conditions, to give excellent overall yields of enantiopure ethyl ketones. The chelating ability of α-OBn amides (and even of α-O-TBS amides, which has been demonstrated by NMR to be better than that of N-OMe amides) accounts for the performance of the approach.