193953-58-1

Upstream product

• 193953-54-7 (3aS,8aR)-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one 
• 501-52-0 3-Phenylpropionic acid 
• 198962-80-0 3-Phenyl-propionic acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester 
• 60656-87-3 benzyloxyacetoaldehyde 
• 336182-92-4 (2S,3S)-2-Benzyl-4-benzyloxy-3-hydroxy-butyric acid (S)-3-phenyl-2-(toluene-4-sulfonylamino)-propyl ester 
• 198962-87-7 (2S,3S)-2-Benzyl-4-benzyloxy-3-hydroxy-butyric acid (1S,2R)-1-(toluene-4-sulfonylamino)-indan-2-yl ester 
• 193953-55-8 (3aS,8aR)-3-((2S,3S)-2-Benzyl-4-benzyloxy-3-hydroxy-butyryl)-3,3a,8,8a-tetrahydro-indeno[1,2-d]oxazol-2-one 

Downstream Products

• 193953-56-9 (4S,5S)-4-benzyl-5-benzyloxymethyl-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Ester derived titanium enolate aldol reaction: Chelation controlled diastereoselective synthesis of syn-aldols

A chelation controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of commercially available L-phenylalaninol derived esters with a variety of bidentate oxyaldehydes proceeded with excellent syn-diastereoselectivities and isolated yields.

Transition-state mimetics for HIV protease inhibitors: Stereocontrolled synthesis of hydroxyethylene and hydroxyethylamine isosteres by ester- derived titanium enolate syn and anti-aldol reactions

Stereocontrolled syntheses of hydroxyethylene dipeptide isostere and aminoalkyl epoxides for hydroxyethylamine isosteres are described. The stereochemistry of both stereogenic centers of the aminoalkyl epoxides 10 and 15 as well as they γ-lactone 17 was assembled by our recently developed highly selective ester-derived titanium enolate aldol reactions. The Ti- enolate of 6 reacted with (benzyloxy)acetaldehyde and cinnamaldehyde to provide the syn-aldol product 7 and anti-aldol product 12, respectively. Removal of the chiral template followed by Curtius rearrangement of the resulting acid provided the desired amine functionality. The present syntheses represent practical and enantioselective entry to a range of other dipeptide isosteres, which are not limited to amino acid derived substituents.

Ester derived titanium enolate aldol reaction: Highly diastereoselective synthesis of syn- and anti-aldols

Aldol reactions of bidentate aldehydes and cis-1-arylsulfonamido-2-indanyl ester derived titanium enolates proceed with excellent syn-diastereoselectivities and good to excellent isolated yields.