A facile synthesis of optically pure amines by reduction of N-acyl-.ALPHA.-methoxyalkylamines derived from .ALPHA.-amino acids using triethylsilane.

Non-Kolbe electrolysis of N-protected-α-amino acids: a standardized method for the synthesis of N-protected (1-methoxyalkyl)amines

“…However, the described methods were initially limited to relatively simple N-acyl-a-amino acids, such as derivatives of glycine, alanine, valine, leucine, phenylalanine, or proline. [20][21][22] Next, the reaction was expanded to more complex compounds, such as oxazolidine-2-one-4-carboxylic acids derived from threonine, 23 2,5-piperazinediones derived from aminomalonic acid, 24 and di-, tri-, or tetrapeptides. 25 From 2000-2003, the Matsumura and Onomura groups applied this electrochemical process for the stereoselective functionalization of N,O-acetals derived from serine.…”

Synthetic Studies on the Sulfur-Cross-Linked Core of Antitumor Marine Alkaloid, Discorhabdins: Total Synthesis of Discorhabdin A

“…Thus, we examined an alternative route via N , O ‐acetal 8 , which could be readily prepared by oxidative decarboxylation of 7 . Consequently, the anodic oxidation7 (graphite anode/graphite cathode system in a nondivided cell) of 7 proceeded smoothly in MeOH in the presence of 5 mol % NaOMe to give 8 in 60 % yield. In contrast, chemical oxidation reactions using Pb(OAc) 4 , PhI(OAc) 2 (PIDA), or PIFA afforded 8 only in low to moderate yields.…”

Ionic and Organometallic‐Catalyzed Organosilane Reductions

“…521 A solution of N -acetyl-2-methoxy-4-tert-butyldimethylsiloxy)pyrrolidine (2 mmol) and Et 3 SiH (4 mmol) in dry CH 2 Cl 2 (3 mL) was treated with BF 3 •OEt 2 (4 mmol) at −40 • . The reaction was monitored by TLC (1-2 hours).…”