Optimized Syntheses of Optically Pure P-Alkene Ligands: Crystal Structures of a Pair of P-Stereogenic Diastereomers
Herrera AC, Linden A, Heinemann FW, Brachvogel RC, von Delius M, Dorta R (2016)
Publication Status: Published
Publication Type: Journal article
Publication year: 2016
Journal
Publisher: GEORG THIEME VERLAG KG
Book Volume: 48
Pages Range: 1117-1121
Journal Issue: 8
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.
Authors with CRIS profile
Alberto Cesar Herrera
Professur für Anorganische Chemie
Frank Wilhelm Heinemann
Lehrstuhl für Anorganische und Allgemeine Chemie
Rene-Chris Brachvogel
Lehrstuhl für Anorganische und Allgemeine Chemie
Max von Delius
Lehrstuhl für Organische Chemie II
Romano Dorta
Professur für Anorganische Chemie
Involved external institutions
Switzerland (CH)How to cite
APA:
Herrera, A.C., Linden, A., Heinemann, F.W., 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://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.
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