Synthesis of Allylic and Propargylic Primary Amines by Reaction of Organometallic Reagents with α-Amidoalkyl Sulfones

Catalytic asymmetric addition of diorganozinc reagents to N -phosphinoylalkylimines

“…The method involves the use of a leaving group (LG) on the ␣-carbon of the N-protected amine. Several leaving groups including benzotriazolates (29), sulfinates (30), and succinimidates (31) have been used for the in situ preparation of N-acylimines.…”

A Practical, One‐Pot Multicomponent Synthesis of α‐Amidosulfides and Their Application as Latent N‐Acylimines in the Friedel–Crafts Reaction

“…On the other hand, benzaldehyde failed to participate in this one-pot procedure, due to problems inherent to the synthesis of aromatic α-amidosulfones from phenylsulfinic acid 6. Nevertheless, using presynthesized α-amidosulfones 7 (aromatic aldehyde, benzyl-carbamate, sodium phenylsulfinate, formic acid/water) [14] expected amidosulfides 4 were isolated in excellent yields (Table 2, Entries 16-19). Table 2.…”

Mannich-type Reactions of in Situ Generated N-Acyliminium Ions from α-Amido p-Tolylsulfones with Silyl Enolates

“…7 The 1 H NMR (600 MHz) and 13 C NMR (150 MHz) spectra were recorded with Varian VNS600 spectrometer. Chemical shifts were reported in ppm in CDCl 3 with tetramethylsilane as the internal standard.…”

“…7, 158.8, 155.7, 136.4, 131.2, 128.6, 128.3, 127.90, 127.86, 113.3, 66.5, 61.5, 55.0, 51.8, 46.6, 24.4, 22.3 7,155.7,137.1,136.4,136.1,128.7,128.3,128.0,027.9,127.5,66.6,61.8,51.8,46.5,24.4,22.4,20.9;MS (EI) 155.8, 137.8, 136.3, 133.4, 129.1, 128.4, 128.3, 128.08, 128.05, 66.8, 61.7, 52.0, 46.3, 24.7, 22.5 157.5, 156.2, 148.9, 136.5, 136.1, 128.4, 128.0, 123.3, 122.6, 66.8, 61.5, 51.9, 46.8, 22.8, 22.5 …”