Stereoselective syntheses of (+)-isoretronecanol and (+)-5-epi-tashiromine via addition of chiral titanium(IV) enolates to cyclic N-acyliminium ions was written by Pereira, Elaine;de Fatima Alves, Conceicao;Bockelmann, Maria Alice;Pilli, Ronaldo A.. And the article was included in Quimica Nova in 2008.Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione This article mentions the following:
The stereoselective addition of the titanium (IV) enolates derived from (S)-4-isopropyl-N-4-chlorobutyryl-1,3-thiazolidine-2-thione and from (S)-4-isopropyl-N-4-chloropentanoyl-1,3-thiazolidine-2-thione to N-Boc-2-methoxypyrrolidine afforded the addition products (+)-I [R = (CH2)2Cl, (CH2)3Cl, resp.] in 84% yield in both cases, as 8.6:1 and 10:1 diastereoisomeric mixtures, resp. A three-step sequence allowed to convert these adducts to (+)-isoretronecanol and (+)-5-epi-tashiromine II [X = CH2, (CH2)2, resp.] in 43% and 49% overall yield, resp. In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione).
(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. The thiazolidine ring is a cyclic N,S acetal, and most syntheses of perhydrothiazolo [3,2-a]pyridines construct the five-membered ring by condensation of aldehydes or ketones either as such or masked. Thiazolidines have been applied as prodrug derivatives for various steroids containing a 3-carbonyl group to improve their topical anti-inflammatory activity. Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione
Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com