Recent advances in the preparation and application of allylboron species in organic synthesis

C Diner, KJ Szabo - Journal of the American Chemical Society, 2017 - ACS Publications
Recent Advances in the Preparation and Application of Allylboron Species in Organic Synthesis |
Journal of the American Chemical Society ACS ACS Publications C&EN CAS Find my institution …

Cationic tricoordinate boron intermediates: borenium chemistry from the organic perspective

TS De Vries, A Prokofjevs, E Vedejs - Chemical Reviews, 2012 - ACS Publications
1. INTRODUCTION The focus of this review is on the reactivity of cationic, tricoordinated
boron electrophiles and on recent applications that rely on intermediates having sextet …

Catalytic asymmetric umpolung allylation of imines

J Liu, CG Cao, HB Sun, X Zhang… - Journal of the American …, 2016 - ACS Publications
Here we report an iridium-catalyzed asymmetric umpolung allylation of imines as a general
approach to prepare 1, 4-disubstituted homoallylic amines, a fundamental class of …

Synthesis of adjacent quaternary stereocenters by catalytic asymmetric allylboration

R Alam, T Vollgraff, L Eriksson… - Journal of the American …, 2015 - ACS Publications
Allylboration of ketones with γ-disubstituted allylboronic acids is performed in the presence
of chiral BINOL derivatives. The reaction is suitable for single-step creation of adjacent …

Development of α, α-disubstituted crotylboronate reagents and stereoselective crotylation via Brønsted or Lewis acid catalysis

S Gao, M Duan, Q Shao, KN Houk… - Journal of the American …, 2020 - ACS Publications
The development of α, α-disubstituted crotylboronate reagents is reported. Chiral Brønsted
acid-catalyzed asymmetric aldehyde addition with the developed E-crotylboron reagent …

Highly diastereo-and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters

JLY Chen, HK Scott, MJ Hesse, CL Willis… - Journal of the …, 2013 - ACS Publications
Readily available, α-substituted allyl/crotyl pinacol boronic esters often give low E/Z
selectivity (with Z favored) in reactions with aldehydes. We found that addition of n BuLi to …

Enantioselective Synthesis of Allylboronates and Allylic Alcohols by Copper‐Catalyzed 1, 6‐Boration

Y Luo, ID Roy, AGE Madec… - Angewandte Chemie …, 2014 - Wiley Online Library
Chiral secondary allylboronates are obtained in high enantioselectivities and 1, 6: 1, 4 ratios
by the copper‐catalyzed 1, 6‐boration of electron‐deficient dienes with bis (pinacolato) …

Biorelevant metals in sustainable metal catalysis—a survey

MS Holzwarth, B Plietker - ChemCatChem, 2013 - Wiley Online Library
A growing world population and increasing energy demands are without a doubt the most
important challenges for mankind within this century. Catalysis is a key technology in various …

Accessing both retention and inversion pathways in stereospecific, nickel-catalyzed Miyaura borylations of allylic pivalates

Q Zhou, HD Srinivas, S Zhang… - Journal of the American …, 2016 - ACS Publications
We have developed a stereospecific, nickel-catalyzed Miyaura borylation of allylic pivalates,
which delivers highly enantioenriched α-stereogenic γ-aryl allylboronates with good yields …

Application of Vinyl Nucleophiles in Matteson Homologations

T Kinsinger, U Kazmaier - Organic Letters, 2022 - ACS Publications
The Matteson homologation with vinyl nucleophiles was found to be a versatile tool for the
synthesis of highly substituted and functionalized allyl boronic esters. High yields and …