In 2013,Ishida, Naoki; Shimamoto, Yasuhiro; Yano, Takaaki; Murakami, Masahiro published 《1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams》.Journal of the American Chemical Society published the findings.Quality Control of Azetidin-3-ol hydrochloride The information in the text is summarized as follows:
In the presence of [Rh(COD)(OH)]2 and the nonracemic bibenzodioxolediphosphine (R)-difluorphos, 1-arylsulfonyl-3-aryl-3-azetidinols such as I (R = Ph, 4-MeOC6H4, 4-F3CC6H4; Ts = 4-MeC6H4SO2) underwent enantioselective rearrangement to give fused thiazinediones such as II (R = Ph, 4-MeOC6H4, 4-F3CC6H4) in 90-95% yields and in 91:9-93:7 er. Stereoselective rearrangement of nonracemic amino acid-derived 1-arylsulfonyl-3-aryl-3-azetidinols such as III (R1 = Ph, 4-MeOC6H4, 4-F3CC6H4; R2 = Me, Me2CH, MeSCH2CH2; R3 = H, Me, MeO, F3C; R4 = H, Me) in the presence of racemic 2,2′-bis{bis(3,5-xylyl)phosphino}-1,1′-binaphthyl yielded fused dihydrohydroxythiazinediones such as IV (R1 = Ph, 4-MeOC6H4, 4-F3CC6H4; R2 = Me, Me2CH, MeSCH2CH2; R3 = H, Me, MeO, F3C; R4 = H, Me) as single diastereomers and enantiomers in 97-99% yields. Rearrangement of I (R = Ph) with a perdeuterated tosyl group yielded a deuterated product monolabeled at the N-Me group; a mechanism for the rearrangement is proposed. The structure of IV (R1 = Ph; R2 = Me; R3 = Me; R4 = H) was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, Azetidin-3-ol hydrochloride(cas: 18621-18-6Quality Control of Azetidin-3-ol hydrochloride)
Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Quality Control of Azetidin-3-ol hydrochloride Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.
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