263764-32-5

Upstream product

• 107-02-8 acrolein 
• 263764-23-4 (S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione 
• 63-91-2 L-phenylalanine 
• 3182-95-4 L-Phenylalaninol 
• 171877-39-7 (S)-4-benzylthiazolidin-2-thione 

Relevant academic research and scientific papers

Stereoselective preparation of C1-C10 and C11-O14 fragments of narbonolide: Exploiting the versatility of thiazolidinethione chiral auxiliary

An efficient stereoselective synthesis of the C1-C10 and C11-O14 fragments of narbonolide, have been accomplished by using a thiazolidinonethione as chiral auxiliary. The stereocenters at C2, C3, C4, C5, C8, and C9 in C1-C10 fragment and C12 and C13 in C1

Studies towards the total synthesis of narbonolide: stereoselective preparation of the C1-C10 fragment

An efficient stereoselective synthesis of the C1-C10 fragment of narbonolide is reported. The stereocentres at C2, 3, 4, 5, 8 and 9 in fragment 5 can be generated via an iterative asymmetric acyl-thiazolidinethione aldol reaction, whereas the stereocentre

Enantioselective total synthesis of (+)-SCH 351448

A stereoselective synthesis of SCH 351448 has been completed. Twelve of the fourteen stereogenic centers were established through chiral enolate reactions, and six key C-C bonds were formed by metathesis reactions.

Asymmetric aldol additions: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones

Asymmetric aldol additions using chlorotitanium enolates of N-acyloxazolidinone, oxazolidinethione, and thiazolidinethione propionates proceed with high diastereoselectivity for the Evans or non-Evans syn product depending on the nature and amount of the base used. With 1 equiv of titanium tetrachloride and 2 equiv of (-)-sparteine as the base or 1 equiv of (-)-sparteine and 1 equiv of N-methyl-2-pyrrolidinone, selectivities of 97:3 to >99:1 were obtained for the Evans syn aldol products using N-propionyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones. The non-Evans syn aldol adducts are available with the oxazolidinethione and thiazolidinethiones by altering the Lewis acid/amine base ratios. The change in facial selectivity in the aldol additions is proposed to be a result of switching of mechanistic pathways between chelated and nonchelated transition states. The auxiliaries can be reductively removed or cleaved by nucleophilic acyl substitution. Iterative aldol sequences with high diastereoselectivity can also be accomplished.

Titanium Enolates of Thiazolidinethione Chiral Auxiliaries: Versatile Tools for Asymmetric Aldol Additions

formula presented Asymmetric aldol additions using chlorotitanium enolates of thiazolidinethione propionates proceed with high diastereoselectivity for the "Evans" or "non-Evans" syn product depending on the nature and amount of the base used. With (-)-sparteine as the base, selectivities of 97:3 to > 99:1 were obtained for the Evans syn products with 2 equivalents of base and for the non-Evans syn when 1 equiv of base was employed. The thiazolidinethione auxiliaries are easily removed, and the aldol adducts can be readily transformed to various functional groups. Even direct reduction to the aldehyde with diisobutylaluminum hydride is possible.