Asymmetric catalytic rearrangements with α-diazocarbonyl compounds

S Dong, X Liu, X Feng - Accounts of Chemical Research, 2022 - ACS Publications
Conspectus α-Diazocarbonyl compounds serve as nucleophiles, dipoles, carbene
precursors, and rare electrophiles, enabling a vast array of organic transformations under …

Modern organic synthesis with α-diazocarbonyl compounds

A Ford, H Miel, A Ring, CN Slattery, AR Maguire… - Chemical …, 2015 - ACS Publications
In 1994, Ye and McKervey published a paper in Chemical Reviews entitled “Organic
Synthesis with α-Diazocarbonyl Compounds”. 1 Our intention then was to draw attention to …

Highly enantioselective carbene insertion into N–H bonds of aliphatic amines

ML Li, JH Yu, YH Li, SF Zhu, QL Zhou - Science, 2019 - science.org
Aliphatic amines strongly coordinate, and therefore easily inhibit, the activity of transition-
metal catalysts, posing a marked challenge to nitrogen-hydrogen (N–H) insertion reactions …

Cycloaddition reactions of enoldiazo compounds

QQ Cheng, Y Deng, M Lankelma… - Chemical Society Reviews, 2017 - pubs.rsc.org
Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition
reactions that allow highly efficient construction of various carbocycles and heterocycles …

The [3+ 3]-cycloaddition alternative for heterocycle syntheses: catalytically generated metalloenolcarbenes as dipolar adducts

X Xu, MP Doyle - Accounts of Chemical Research, 2014 - ACS Publications
Conspectus The combination of two or more unsaturated structural units to form cyclic
organic compounds is commonly referred to as cycloaddition, and the combination of two …

[HTML][HTML] Chemoselective carbene insertion into the N−H bonds of NH3·H2O

Z Liu, Y Yang, Q Song, L Li, G Zanoni, S Liu… - Nature …, 2022 - nature.com
The conversion of inexpensive aqueous ammonia (NH3· H2O) into value-added primary
amines by N− H insertion persists as a longstanding challenge in chemistry because of the …

Chiral proton-transfer shuttle catalysts for carbene insertion reactions

YY Ren, SF Zhu, QL Zhou - Organic & Biomolecular Chemistry, 2018 - pubs.rsc.org
Transition metal-catalyzed carbene insertion into X–H bonds (X= N, O, S, and C) represents
a typical carbene transfer reaction and has been widely used in organic synthesis. The …

[HTML][HTML] Visible-light-induced organocatalytic enantioselective N–H insertion of α-diazoesters enabled by indirect free carbene capture

W Guo, Y Zhou, H Xie, X Yue, F Jiang, H Huang… - Chemical …, 2023 - pubs.rsc.org
While asymmetric insertion of metal carbenes into H–X (X= C, N, O, etc.) bonds has been
well-established, asymmetric control over free carbenes is challenging due to the presence …

A Spiro Phosphamide Catalyzed Enantioselective Proton Transfer of Ylides in a Free Carbene Insertion into N− H Bonds

JB Pan, XG Zhang, YF Shi, AC Han… - Angewandte Chemie …, 2023 - Wiley Online Library
Free carbene readily causes multiple side reactions due to its high energy, thus its
asymmetric transformation is very difficult. We present here our findings of high‐pKa …

Enantioselective Palladium‐Catalyzed Carbene Insertion into the N− H Bonds of Aromatic Heterocycles

V Arredondo, SC Hiew, ES Gutman… - Angewandte Chemie …, 2017 - Wiley Online Library
C3‐substituted indoles and carbazoles react with α‐aryl‐α‐diazoesters under palladium
catalysis to form α‐(N‐indolyl)‐α‐arylesters and α‐(N‐carbazolyl)‐α‐arylesters. The …