33266-05-6Relevant academic research and scientific papers
Studies of π-diastereofacial selectivity: The influence of α- oxathiolane ketals on cyclic ketones
Dimitroff, Martin,Fallis, Alex G.
, p. 2527 - 2530 (1998)
The facial influence and synthetic utility of oxygen and sulfur heteroatoms adjacent to carbocyclic ketones upon nucleophilic addition has been investigated. Addition to the carbonyl group displayed a preference for attack anti to sulfur and syn to oxygen in synthetically useful ratios. Diisopropylaluminum hydride reduction in the cyclopentanone series reversed this facial preference.
Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides
Bartolo, Nicole D.,Demkiw, Krystyna M.,Read, Jacquelyne A.,Valentín, Elizabeth M.,Yang, Yingying,Dillon, Alexandra M.,Hu, Chunhua T.,Ward, Michael D.,Woerpel
, p. 3042 - 3065 (2022/02/25)
The addition of the highly reactive reagent allylmagnesium halide to α-substituted acyclic chiral ketones proceeded with high stereoselectivity. The stereoselectivity cannot be analyzed by conventional stereochemical models because these reactions do not conform to the requirements of those models. Instead, the stereoselectivity arises from the approach of the nucleophile to the most accessible diastereofaces of the lowest-energy conformations of the ketones. High stereoselectivity is expected, and the stereochemical outcome can be predicted, with conformationally biased ketones that have sterically distinguishable diastereofaces wherein only one face is accessible for nucleophilic addition. The conformations of the ketones can be determined by a combination of computational modeling and, in some cases, structure determination by X-ray crystallography.
On the Reaction of Thioacetals with Sulphuryl Chloride
Bulman-Page, Philip C.,Ley, Steven V.,Morton, Judith A.,Williams, David J.
, p. 457 - 461 (2007/10/02)
Sulphuryl chloride reacts with 1,3-oxathiolans and 1,3-dithiolans to afford unstable intermediate trans-2,3-dichloro-1,4-oxathians or trans-2,3-dichloro-1,4-dithians.Some of these intermediates can be converted on hydrolytic work up to α-ketothioacetals in reasonable yield.Intermediates in the rearrangement pathway have been identified.Reaction of 6-oxospiro (4) with toluene-p-sulphonic acid gave 2,14-dioxa-11-thiatetracyclo1,10.03,8>heptadec-3-en-4-one (20), a novel tetracyclic compound whose structure was determined by X-ray crystallography.
