Recent Advances in Catalytic Asymmetric Synthesis of Tertiary Alcohols via Nucleophilic Addition to Ketones

YL Liu, XT Lin - Advanced Synthesis & Catalysis, 2019 - Wiley Online Library
Chiral tertiary alcohols are an important class of organic compounds which have found wide
applications in both academia and industry. Therefore, various synthetic strategies towards …

Electroreductive olefin–ketone coupling

P Hu, BK Peters, CA Malapit… - Journal of the …, 2020 - ACS Publications
A user-friendly approach is presented to sidestep the venerable Grignard addition to
unactivated ketones to access tertiary alcohols by reversing the polarity of the disconnection …

CuH-catalyzed enantioselective ketone allylation with 1, 3-dienes: scope, mechanism, and applications

C Li, RY Liu, LT Jesikiewicz, Y Yang, P Liu… - Journal of the …, 2019 - ACS Publications
Chiral tertiary alcohols are important building blocks for the synthesis of pharmaceutical
agents and biologically active natural products. The addition of carbon nucleophiles to …

Conjugated ynones in catalytic enantioselective reactions

L Wang, H Zhu, T Peng, D Yang - Organic & Biomolecular Chemistry, 2021 - pubs.rsc.org
Conjugated ynones are easily accessible feedstock and the existence of an alkyne bond
endows ynones with different attractive reactivities, thus making them unique substrates for …

Enantioselective allylation using allene, a petroleum cracking byproduct

RY Liu, Y Zhou, Y Yang… - Journal of the American …, 2019 - ACS Publications
Allene (C3H4) gas is produced and separated on million-metric-ton scale per year during
petroleum refining but is rarely employed in organic synthesis. Meanwhile, the addition of an …

A regio-and enantioselective CuH-catalyzed ketone allylation with terminal allenes

EY Tsai, RY Liu, Y Yang… - Journal of the American …, 2018 - ACS Publications
We report a method for the highly enantioselective CuH-catalyzed allylation of ketones that
employs terminal allenes as allylmetal surrogates. Ketones and allenes bearing diverse and …

Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation

S Xie, D Li, H Huang, F Zhang… - Journal of the American …, 2019 - ACS Publications
The intermolecular radical addition to the carbonyl group is difficult due to the facile
fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to …

Ligand-controlled diastereodivergent, enantio-and regioselective copper-catalyzed hydroxyalkylboration of 1, 3-dienes with ketones

JJ Feng, Y Xu, M Oestreich - Chemical Science, 2019 - pubs.rsc.org
A copper-catalyzed three-component coupling of 1, 3-dienes, bis (pinacolato) diboron, and
ketones allows for the chemo-, regio-, diastereo-and enantioselective assembly of densely …

Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and …

FW van der Mei, C Qin, RJ Morrison… - Journal of the …, 2017 - ACS Publications
A practical method for enantioselective synthesis of fluoroalkyl-substituted Z-homoallylic
tertiary alcohols has been developed. Reactions may be performed with ketones containing …

Chiral Phosphoric Acid Dual‐Function Catalysis: Asymmetric Allylation with α‐Vinyl Allylboron Reagents

S Gao, M Duan, KN Houk… - Angewandte Chemie …, 2020 - Wiley Online Library
We report a dual function asymmetric catalysis by a chiral phosphoric acid catalyst that
controls both enantioselective addition of an achiral α‐vinyl allylboronate to aldehydes and …