• Journal of the Korean Chemical Society
• /
• v.33 no.4
• /
• pp.426-430
• /
• 1989

Amino alcohol-derived thiazolidinethiones [4-(S)-IPTT, 4(S)-ETT] serve as efficient chiral auxiliary in tin medicated aldol condensation. A highly enantioselective aldol-type reaction forming various ${\beta}$-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehyde is achieved via divalent tin enolate. The other advantages of these chiral auxiliaries were the ease of removal by methanolysis.

• Journal of the Korean Chemical Society
• /
• v.32 no.6
• /
• pp.588-592
• /
• 1988

A chiral recognition was observed in aminolysis of 3-acyl-4(S)-isopropyl-1,3-thiazolidine-2-thione by racemic amine to give an optically active amide (S-excess) and amine (R-excess). This procedure can be applied to synthesis of macrocyclic diamide macrocyclic spermidine alkaloid, and peptide. The rate of this aminolysis is remarkably affected by steric surrounding; completion of reaction can be easily judged by the disappearance of the original yellow color of 4(S)-AITT. These features of the aminolysis suggested a potential recognition racemic amines by a chiral 4 (S)-AITT derivative. Thus 4 (S)-AITT was synthesized from 4 (S)-isopropyl-1, 3-thiazolidine-2-thione and carboxylic acids.

• Applied Chemistry for Engineering
• /
• v.9 no.6
• /
• pp.914-919
• /
• 1998

Optically pure $C_2-Symmetric$ pyrrolidine amides (8) were synthesized from readily available 1,2:5,6-di-O-isopropylidene-D-mannitol (1). Cyclization of dimesylated hexitol (4) with benzyl amine gave an inseparable mixture of $C_2-Symmetric$ pyrrolidine amine derivative (5) as a major product, concurring with its cis isomer (6) as a minor product. The pyrrolidine amines (5,6) were converted to separable pyrrolidine amides (8,9) via free amine (7). Optical purity of desired $C_2-Symmetric$ pyrrolidine amide (8a) was determined with its Mosher derivatives (13,14) by their $^1H$ and $^{19}F$ NMR spectra.

• The Journal of the Convergence on Culture Technology
• /
• v.7 no.2
• /
• pp.389-394
• /
• 2021

In this work, we study the properties of molecular structure and boundary orbital functions of the DPHMP-AlH and propiophenone and butyrophenone, which are forms of alkoxy-amine-aluminum derivatives. Furthermore, we investigate the effect on the selective reduction of the final products (R), (S)-phenylpropanol and (R), (S)-phenylbutanol by calculating the stereoscopic and thermodynamic parameters of the transition state. Considering the three-dimensional molecular structural stability, the transition status of (S) types DPHMP-AlH and alkylphenone was found to be more stable, resulting in the selective reductions of DPHM-AlH and alkylphenone from this result: (S)-(1)-phenylpropanol and (S)-(1)-phenylbutanol was confirmed that the formation was advantageous.