Literature DB >> 25530612

π-Helicenes truncated to a minimum: access through a domino approach involving multiple carbopalladations and a Stille coupling.

Bastian Milde1, Markus Leibeling, Martin Pawliczek, Jörg Grunenberg, Peter G Jones, Daniel B Werz.   

Abstract

A novel type of π-helicenes is reported, in which the π-system is truncated to an all-s-cis all-Z oligoene chain. A domino sequence was developed, consisting of up to four consecutive carbopalladation reactions and a terminal Stille cross-coupling, to generate these entities in one step from the respective linear oligoynes. Despite the minimal π-system, very high optical rotation values were encountered for the single enantiomers. X-ray crystallography confirmed their screw-shaped structure.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbopalladation; domino reaction; helicenes

Year:  2014        PMID: 25530612     DOI: 10.1002/anie.201408637

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  3 in total

1.  Ynamide carbopalladation: a flexible route to mono-, bi- and tricyclic azacycles.

Authors:  Craig D Campbell; Rebecca L Greenaway; Oliver T Holton; P Ross Walker; Helen A Chapman; C Adam Russell; Greg Carr; Amber L Thomson; Edward A Anderson
Journal:  Chemistry       Date:  2015-07-16       Impact factor: 5.236

2.  Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones.

Authors:  Valeria Nori; Antonio Arcadi; Armando Carlone; Fabio Marinelli; Marco Chiarini
Journal:  Beilstein J Org Chem       Date:  2020-05-20       Impact factor: 2.883

3.  Spatiotemporal Mapping of Efficient Chiral Induction by Helicene-Type Additives in Copolymer Thin Films.

Authors:  Marius Morgenroth; Mirko Scholz; Laure Guy; Kawon Oum; Thomas Lenzer
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-23       Impact factor: 16.823

  3 in total

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