Stereoselective Hydrocoupling of Optically Active 3-trans-Cinnamoyloxazolidinones by Electroreduction was written by Kise, Naoki;Mashiba, Syun-ichiro;Ueda, Nasuo. And the article was included in Journal of Organic Chemistry in 1998.Related Products of 76186-04-4 This article mentions the following:
Reductive hydrocoupling of chiral 3-trans-cinnamoyloxazolidinones was studied by an electrochem. method. The electroreduction was performed conveniently at a constant current using an undivided cell. The stereoselectivity of the hydrodimers was strongly affected by the electrolyte employed. Electroreduction of (S)-4-isobutyl-3-trans-cinnamoyloxazolidinone (I) in 0.3 M Et4NOTs/AN gave a mixture of two diastereomers of all-trans cyclized hydrodimer, and the selectivity was R,S,R/S,R,S = 85:15. On the other hand, the reduction of I in 1.7 M LiClO4/THF afforded a diastereomeric mixture of hydrodimers in a selectivity of R,R/S,S/R,S = 5:52:43. The stereoselectivities were explained by considering stable conformations of intermediate anion radicals, i.e., syn-Z type for naked anion radicals and anti-Z type for lithiated anion radicals. Semiempirical calculations also supported this hypothesis. Electroreductions of (S)-4-isobutyl-3-cis-cinnamoyloxazolidinone and (S)-4-isobutyl-3-phenylpropioloyloxazolidinone gave the same stereoselectivity as electroreduction of I did. The electroreductive hydrocoupling was not inhibited by para and meta substitution on the aryl group of 3-trans-cinnamoyloxazolidinones. An ortho substitution, however, hindered the hydrocoupling and lowered the stereoselectivity of the hydrodimers. Electroreduction of 3-trans-cinnamoyloxazolidinethione and thiazolidinethione gave trans-3,4-diphenylcyclopentanone as a product, and the stereoselectivities were similar to that obtained from the corresponding oxazolidinone. In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4Related Products of 76186-04-4).
(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. Thiazolidine is an important scaffold and has a wide range of promising biological activities. Thiazolidine derivatives have reported anti-inflammatory and anti-nociceptive activity. Thiazolidines have been applied as prodrug derivatives for various steroids containing a 3-carbonyl group to improve their topical anti-inflammatory activity. Related Products of 76186-04-4
Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com