Reduction of Phthalimides with Sodium Borohydride

Mechanistic Studies on the Organocatalytic α‐Chlorination of Aldehydes: The Role and Nature of Off‐Cycle Intermediates

“…In a 1 HNMR study,t he influence of the Cl + sources 19 and 20 on aminal formation was studied ( Figure 6). As expected, the electron-rich Me 4 (hydrocinnamaldehyde, NCP, 2), phthalimide was cleaved upon workup with NaBH 4 [14] ), 9 (heptanedial, NCS, 2). Finally,the effects of acids as additives was investigated.…”

Enantioselective Aza‐Michael Addition of Imides by Using an Integrated Strategy Involving the Synthesis of a Family of Multifunctional Catalysts, Usage of Multiple Catalysis, and Rational Design of Experiment

“…As was anticipated, compound 3 a was both chemically and configurationally unstable, so to determine the yield and reaction enantioselectivity, the reaction mixture obtained employing catalyst II was treated with NaBH 4 and product 4 a bearing two additional stereocenters, was obtained as single isolated (major) stereoisomer with 70 % ee and in 62 % yield (Table 1, entry 1, and the Supporting Information). [7] A class of sever-al trifunctional amino acid-thiourea catalysts (III a-h) [8] performing with comparable conversion, gave higher enantioselectivities (up to 77 % ee employing catalysts III b or III e) with respect to catalyst II.…”

Mechanistic Studies on the Organocatalytic α‐Chlorination of Aldehydes: The Role and Nature of Off‐Cycle Intermediates

“… Crystal structures of isolated intermediates: 5 (hydrocinnamaldehyde, NCS, 2 ), 6 (octanal, NCS, 2 ), 7 (pentanal, NCS, 2 ), 8 (hydrocinnamaldehyde, NCP, 2 ), phthalimide was cleaved upon workup with NaBH 4 ), 9 (heptanedial, NCS, 2 ).…”