Preparation of Racemic and Optically Active Trifluoromethyl Aziridines and Azetidines

A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis.

A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50-73% overall yields and 88-94% ee, and azetidines in 22-32% overall yields a...

Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline

Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction.

A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining β-amino esters as a key step. These β-amino esters on subsequent reduction followed by TsCl/KOH mediated cyclization produced the corresponding racemic and non-racemic azetidines with high yi...

Computational study in Regioselectivie Synthesis of New Spiro-oxindolopyrrolidines

One-pot, four-component procedure for the synthesis of a small library of new chiral spiro- oxindolopyrrolidines with high regio-, diastereo- (>99:1 dr), and enantioselectivity (up to 80% ee) is described. In this process, the regio- and stereochemical 1,3-dipolar cycloaddition of azomethine ylides, which were generated insitu by the reaction of isatin derivatives and sarcosin,with optically ac...

Access to novel functionalized trifluoromethyl β-lactams by ring expansion of aziridines.

From carboxylic acid trifluoromethyl aziridines, halogeno β-lactams were obtained stereoselectively by ring expansion. Different conditions such as radical, organometallic reactions allowed easy and selective access to CF3-β-lactams substituted at the C-3 position.