Synthesis of Chiral Amines Using α‐Amino Aldehydes

Abstract

O2 can do: Innocuous molecular oxygen O2 is the only reagent needed to perform highly chemoselective biocatalytic single‐step alkene‐cleavage reactions (see scheme). The products are analogous to those of (reductive) ozonization and related metal‐based methods. In contrast neither special equipment nor an additional reducing agent is required. The biocatalytic reaction can be performed at ambient temperature. Depending on the substrate, aldehydes or ketones are obtained.

Preparation of enantiomerically enriched α‐aminoorganostannanes and their applications in stereoselective synthesis

“…The synthesis of chiral amines and related derivatives (i.e., amino acids, amino alcohols) is an important field of research in contemporary chemistry due to the ubiquity of amine functional groups in natural products, pharmaceutical agents, synthetic materials, and catalysts 1–3. Over the last decades, the transmetalation/electrophilic trapping of stereochemically defined α‐aminoorganostannanes has emerged as an attractive transformation for the preparation of chiral functionalized amines (Scheme ).…”

Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

“…The ee's of compounds 7a-b after ketalization showed no appreciable changes when compared with the ee's of compounds 7a-b before the acetal hydrolysis with formic acid. It is worth noting that the very mild procedure to obtain N-protected-a-aminoaldehydes through the corresponding acetal hydrolysis without detectable racemization constitutes a valuable route to these useful chiral building blocks (Jurczak and Golebiowski 1989;Reetz 1999Reetz , 1991Gryko et al 2003;Hili et al 2008;Baktharaman et al 2008;Izawa and Onishi 2006;Garner and Park 1987;Chowdari et al 2003;Tokuyama et al 2002;Dias et al 2003;Kwon and Myers 2005;Wen and Crews 1998;Hili and Yudin 2006;Myers et al 2000;Diness et al 2004). …”

Stereoselective Synthesis of 1,2‐trans‐Diamines Using the Three‐Component Borono‐Mannich Condensation – Reaction Scope and Mechanistic Insights

“…Herein, we report the details of an efficient trans ‐selective synthesis of enantioenriched vicinal diamines through the PBM reactions of N ‐protected α‐amino aldehydes. These substrates are readily accessible but known for their susceptibility to racemization …”