Header

UZH-Logo

Maintenance Infos

Optimized syntheses of optically pure p-alkene ligands: crystal structures of a pair of p-stereogenic diastereomers


Dorta, Romano; Herrera, Alberto; Linden, Anthony; Heinemann, Frank; Brachvogel, René-Chris; von Delius, Max (2016). Optimized syntheses of optically pure p-alkene ligands: crystal structures of a pair of p-stereogenic diastereomers. Synthesis, 48(08):1117-1121.

Abstract

The ‘privileged’ P-alkene ligand (S)-2 is synthesized on a > 40 gram scale in 96% yield starting from dibenz[b,f]azepine-PCl2 (1; accessible on > 80 g scale) and (S)-BINOL. Similarly, the P-alkenes (R)-3 and
the ‘chiral-at-P’ (SP,SC)-4 are obtained from (R)-Taddol [(R,R)-α,α,α', α'-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol] and (S)-α,α-diphenylprolinol, respectively, in multigram quantities and high purity. The crystal structures of (SP,SC)-4, its diastereomer (RP,SC)-4, and of the(R)-SPINOL-derived ligand (R)-5 are reported. A slightly revised synthesis of SPINOL is also disclosed.

Abstract

The ‘privileged’ P-alkene ligand (S)-2 is synthesized on a > 40 gram scale in 96% yield starting from dibenz[b,f]azepine-PCl2 (1; accessible on > 80 g scale) and (S)-BINOL. Similarly, the P-alkenes (R)-3 and
the ‘chiral-at-P’ (SP,SC)-4 are obtained from (R)-Taddol [(R,R)-α,α,α', α'-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol] and (S)-α,α-diphenylprolinol, respectively, in multigram quantities and high purity. The crystal structures of (SP,SC)-4, its diastereomer (RP,SC)-4, and of the(R)-SPINOL-derived ligand (R)-5 are reported. A slightly revised synthesis of SPINOL is also disclosed.

Statistics

Citations

1 citation in Web of Science®
1 citation in Scopus®
Google Scholar™

Altmetrics

Downloads

3 downloads since deposited on 14 Apr 2016
0 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:synthetic methods, ligand synthesis, chiral ligands
Language:English
Date:2016
Deposited On:14 Apr 2016 16:49
Last Modified:15 Apr 2016 06:10
Publisher:Georg Thieme Verlag
ISSN:0039-7881
Funders:Sigma–Aldrich Chemie GmbH (Buchs, Switzerland), FAU Erlangen-Nürnberg, DFG (Emmy-Noether Programme; m.v.d.), FONACIT (Venezuela)
Publisher DOI:https://doi.org/10.1055/s-0035-1560410

Download

Preview Icon on Download
Content: Published Version
Language: English
Filetype: PDF - Registered users only
Size: 412kB
View at publisher

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations