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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.

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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:08 Dec 2017 19:22
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

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