Diastereoselective synthesis of α-(aminomethyl)-γ-butyrolactones via a catalyst-free aminolactonization

Abstract

An auto-catalytic domino reaction, presumably involving an aza-Michael reaction, proton transfer, and lactonization, furnishing α-(aminomethyl)-γ-butyrolactones in near quantitative yields and excellent diastereoselectivity is described.

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

“…Enynes 2a–2u and the carboxylic acid precursors for the preparation of NHPI esters 1h , 1i , and 1m were synthesized according to previous reports in the literature. − …”

Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates­

“…The following MBH alcohols were prepared by using GP2 and their spectral data correspond with published data: Methyl 2-(hydroxy(phenyl)methyl)acrylate (9′a), 28 methyl 2-(hydroxy(4tolyl)methyl)acrylate (9′b), 28 methyl 2-((4-bromophenyl)(hydroxy)methyl)acrylate (9′c), 28 methyl 2-((4-cyanophenyl)(hydroxy)methyl)acrylate (9′d), 29 methyl 2-((2-bromophenyl)(hydroxy)methyl)acrylate (9′f), 28 methyl 2-((3-bromophenyl)(hydroxy)methyl)acrylate (9′g), 28 benzyl 2-(hydroxy(phenyl)methyl)acrylate (9′i), 29 and tert-butyl 2-(hydroxy(phenyl)methyl)acrylate (9′j). 29…”

Modular Synthesis of ortho‐Thiolated Aryl Esters Enabled with Thiocarbonate through Catellani Strategy

“…First, we used 2‐arylthio aryl ester 3 a as a raw material and successfully obtained the corresponding arylcarboxylic acid derivative 4 a in an alkaline environment [26] . The reduction experiment showed that the ester group could be reduced under mild conditions when LiAlH 4 was used as reducing agent, and the yield of 4 b was 97 % [27] . After that, we tried to use 2‐arylthio aryl ester to synthesize a benzyl isothiazole compound.…”

“…[26] The reduction experiment showed that the ester group could be reduced under mild conditions when LiAlH 4 was used as reducing agent, and the yield of 4 b was 97 %. [27] After that, we tried to use 2-arylthio aryl ester to synthesize a benzyl isothiazole compound. To our delight, 3 a was successfully converted into the ideal product 4 c under the action of ammonium formate and iodobenzene diacetate.…”