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

DOI: 10.1055/s-0035-1560410

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.

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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://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.

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