Enantioselective synthesis of allenes by catalytic traceless petasis reactions

Y Jiang, AB Diagne, RJ Thomson… - Journal of the American …, 2017 - ACS Publications
Allenes are useful functional groups in synthesis as a result of their inherent chemical
properties and established reactivity patterns. One property of chemical bonding renders 1 …

Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols

D Qian, LL Wu, Z Lin, J Sun - Nature Communications, 2017 - nature.com
Although chiral allene preparation via formal SN2'nucleophilic substitutions of
enantioenriched propargylic derivatives or metal-catalyzed reactions of racemic propargylic …

Organocatalytic synthesis of axially chiral tetrasubstituted allenes

TT Nguyen - Organic & Biomolecular Chemistry, 2023 - pubs.rsc.org
Asymmetric organocatalysis is a growing method for the synthesis of axially chiral
tetrasubstituted allenes, the most challenging one among allene syntheses. In this method …

Highly enantioselective synthesis of chiral allenes by sequential creation of stereogenic center and chirality transfer in a single pot operation

M Periasamy, N Sanjeevakumar, M Dalai… - Organic …, 2012 - ACS Publications
Chiral allenes are readily accessed in a single pot operation in the reaction of terminal
alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77 …

Recent advances in the catalytic syntheses of allenes: a critical assessment

RK Neff, DE Frantz - ACS Catalysis, 2014 - ACS Publications
The increasing synthetic utility of allenes in organic synthesis combined with their
incorporation into a growing list of natural products and active pharmaceutical ingredients …

Copper hydride catalyzed enantioselective synthesis of axially chiral 1, 3-disubstituted allenes

L Bayeh-Romero, SL Buchwald - Journal of the American …, 2019 - ACS Publications
The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral
starting materials remains a long-standing challenge in organic synthesis. Here, we report …

Phase-transfer-catalysed asymmetric synthesis of tetrasubstituted allenes

T Hashimoto, K Sakata, F Tamakuni, MJ Dutton… - Nature Chemistry, 2013 - nature.com
Allenes are molecules based on three carbons connected by two cumulated carbon–carbon
double bonds. Given their axially chiral nature and unique reactivity, substituted allenes …

Recent advances in the metal-catalyzed asymmetric synthesis of chiral allenes

W Xiao, J Wu - Organic Chemistry Frontiers, 2022 - pubs.rsc.org
Chiral allenes, which exist widely in natural products, bioactive pharmaceuticals, and
advanced functional materials, have received considerable attention from chemists. They …

Recent applications of chiral allenes in axial-to-central chirality transfer reactions

RK Neff, DE Frantz - Tetrahedron, 2015 - Elsevier
The unique structural architecture of the orthogonal cumulative π-system in allenes has
garnered the attention of synthetic chemists for over a century. 1 From a general reactivity …

A direct synthesis of allenes by a traceless Petasis reaction

DA Mundal, KE Lutz, RJ Thomson - Journal of the American …, 2012 - ACS Publications
A one-pot synthesis of allenes by the 2-nitrobenzenesulfonylhydrazide-mediated coupling of
hydroxyaldehydes or ketones with alkynyl trifluoroborate salts is reported. This mild process …