A General and Selective Rhodium‐Catalyzed Reduction of Amides, N‐Acyl Amino Esters, and Dipeptides Using Phenylsilane

Abstract

This article describes a selective reduction of functionalized amides, including N-acyl amino esters and dipeptides, to the corresponding amines using simple [Rh(acac)(cod)]. The catalyst shows excellent chemoselectivity in the presence of different sensitive functional moieties.

B(C6F5)3‐Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane

“…Although impressive advances in heterogeneous and homogeneous catalytic hydrogenation of amides to amines via CÀO bond scission have been achieved in the past decade (Scheme 1a), [3,4] major disadvantages such as the required harsh conditions (high pressure and elevated temperatures), limited functional group compatibility and difficulty in the control of CÀO bond cleavage selectivity remain to be addressed. Alternatively, catalytic hydrosilyla-tion of amides to amines has been intensively explored due to its convenience and simplicity, [5] and various amides could be smoothly converted into the corresponding amines under the catalysis of precious metals, [6] earth abundant metals [7] and even the simple bases [8] (Scheme 1b). Notably, the boron-based organocatalysts have been successfully applied in this transformation under metal-free conditions.…”

Deal;Photoredox Catalysis for the Cycloaddition Reactions

“…Modern chemical syntheses are completely relying on the atom economical synthesis approach to enhance the sustainability. [1][2][3][4][5][6][7][8][9] Additionally, if the complex and valuable products can be achieved from easily available and cheap starting materials that should significantly increase the valorization potential of the methodology. [10][11][12][13] Based on this consideration, cycloaddition reactions are one of them which offer high valued cyclic products from cheap and easily available starting materials.…”

Reduction of Amides to Amines under Mild Conditions via Catalytic Hydrogenation of Amide Acetals and Imidates

“…These types of pseudodipeptides were previously prepared from dipeptides by selective reduction of dipeptides using BH 3 -THF complex [10] and phenylsilane. [11] The compounds with a reduced peptide bond represents an area of increased interest and have found importance as enzyme inhibitors, antagonists and potential agents for gene delivery. [12] Scheme 1.…”

“…Special attention was focused on reduction of peptide bond in amino acids presenting an alternative method for the synthesis of pseudopeptides containing CH 2 −N amide bond surrogate. These types of pseudodipeptides were previously prepared from dipeptides by selective reduction of dipeptides using BH 3 ‐THF complex and phenylsilane . The compounds with a reduced peptide bond represents an area of increased interest and have found importance as enzyme inhibitors, antagonists and potential agents for gene delivery…”