Increasing the reactivity of amides towards organometallic reagents: an overview

V Pace, W Holzer, B Olofsson - Advanced Synthesis & Catalysis, 2014 - Wiley Online Library
The nucleophilic addition of carbon nucleophiles to amides has traditionally been a difficult
task, both due to reactivity and selectivity problems. When successful, these processes …

Total synthesis of complex alkaloids by nucleophilic addition to amides

T Sato, M Yoritate, H Tajima, N Chida - Organic & biomolecular …, 2018 - pubs.rsc.org
Nucleophilic addition to amides has been recognized as a promising transformation for total
synthesis of complex alkaloids. Amides can accept two different organometallic reagents …

Making Full Use of TMSCF3: Deoxygenative Trifluoromethylation/Silylation of Amides

Y Wang, SJ Li, F Jiang, Y Lan… - Journal of the American …, 2024 - ACS Publications
As one of the most powerful trifluoromethylation reagents,(trifluoromethyl) trimethylsilane
(TMSCF3) has been widely used for the synthesis of fluorine-containing molecules …

Iridium‐Catalyzed Reductive Strecker Reaction for Late‐Stage Amide and Lactam Cyanation

ÁL Fuentes de Arriba, E Lenci… - Angewandte Chemie …, 2017 - Wiley Online Library
A new iridium‐catalyzed reductive Strecker reaction for the direct and efficient formation of α‐
amino nitrile products from a broad range of (hetero) aromatic and aliphatic tertiary amides …

Total Synthesis of (±)‐Gephyrotoxin by Amide‐Selective Reductive Nucleophilic Addition

K Shirokane, T Wada, M Yoritate… - Angewandte …, 2014 - Wiley Online Library
A chemoselective approach for the total synthesis of (±)‐gephyrotoxin has been developed.
The key to success was the utilization of N‐methoxyamides, which enabled the direct …

Iridium-Catalyzed Chemoselective Reductive Nucleophilic Addition to N-Methoxyamides

M Nakajima, T Sato, N Chida - Organic letters, 2015 - ACS Publications
Iridium-catalyzed reductive nucleophilic addition to N-methoxyamides is reported. The
reaction took place in high yields in the presence of a variety of sensitive functional groups …

Nucleophilic addition to N-alkoxyamides

T Sato, N Chida - Organic & Biomolecular Chemistry, 2014 - pubs.rsc.org
An amide group is one of the most abundant functional groups in organic synthesis.
However, nucleophilic addition to amide carbonyls has received less attention than their …

Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, and N‐Methoxyamides

M Nakajima, Y Oda, T Wada… - … A European Journal, 2014 - Wiley Online Library
As the complexity of targeted molecules increases in modern organic synthesis,
chemoselectivity is recognized as an important factor in the development of new …

General One‐Pot Reductive gem‐Bis‐Alkylation of Tertiary Lactams/Amides: Rapid Construction of 1‐Azaspirocycles and Formal Total Synthesis of (±) …

KJ Xiao, JM Luo, XE Xia, Y Wang… - Chemistry–A European …, 2013 - Wiley Online Library
Amides are a class of highly stable and readily available compounds. The amide functional
group constitutes a class of powerful directing/activating and protecting group for C C bond …

A general method for the one-pot reductive functionalization of secondary amides

PQ Huang, YH Huang, KJ Xiao, Y Wang… - The Journal of Organic …, 2015 - ACS Publications
A one-pot reaction for the transformation of common secondary amides into amines with C–
C bond formation is described. This method consists of in situ amide activation with Tf2O …