Optimized Syntheses of Optically Pure P-Alkene Ligands: Crystal Structures of a Pair of P-Stereogenic Diastereomers

Journal article


Publication Details

Author(s): Herrera AC, Linden A, Heinemann F, Brachvogel RC, von Delius M, Dorta R
Journal: Synthesis-Stuttgart
Publisher: GEORG THIEME VERLAG KG
Publication year: 2016
Volume: 48
Journal issue: 8
Pages range: 1117-1121
ISSN: 0039-7881


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' (S-P, S-C)-4 are obtained from (R)-Taddol [(R, R)-alpha, alpha, alpha', alpha'-tetraphenyl- 2,2-dimethyl-1,3-dioxolane-4,5-dimethanol] and (S)-alpha, alpha-diphenylprolinol, respectively, in multigram quantities and high purity. The crystal structures of (S-P, S-C)-4, its diastereomer (R-P, S-C)-4, and of the (R)-SPINOL-derived ligand (R)-5 are reported. A slightly revised synthesis of SPINOL is also disclosed.


FAU Authors / FAU Editors

Brachvogel, Rene-Chris
Lehrstuhl für Anorganische und Allgemeine Chemie
Dorta, Romano Prof. Dr.
Professur für Anorganische Chemie
Heinemann, Frank Dr.
Lehrstuhl für Anorganische und Allgemeine Chemie
Herrera, Alberto Cesar
Professur für Anorganische Chemie
von Delius, Max Dr.
Lehrstuhl für Organische Chemie II


External institutions with authors

Universität Zürich (UZH)


How to cite

APA:
Herrera, A.C., Linden, A., Heinemann, F., Brachvogel, R.-C., von Delius, M., & Dorta, R. (2016). Optimized Syntheses of Optically Pure P-Alkene Ligands: Crystal Structures of a Pair of P-Stereogenic Diastereomers. Synthesis-Stuttgart, 48(8), 1117-1121. https://dx.doi.org/10.1055/s-0035-1560410

MLA:
Herrera, Alberto Cesar, et al. "Optimized Syntheses of Optically Pure P-Alkene Ligands: Crystal Structures of a Pair of P-Stereogenic Diastereomers." Synthesis-Stuttgart 48.8 (2016): 1117-1121.

BibTeX: 

Last updated on 2019-21-07 at 07:59