Display options
Cite
Bader A, Pabel M, Willis AC, et al. First Resolution of a Free Secondary Phosphine Chiral at Phosphorus and Stereospecific Formation and Structural Characterization of a Homochiral Secondary Phosphine-Borane Complex. Inorg Chem. 1996;35(13):3874-3877doi: 10.1021/ic951494h.
Bader, A., Pabel, M., Willis, A. C., & Wild, S. B. (1996). First Resolution of a Free Secondary Phosphine Chiral at Phosphorus and Stereospecific Formation and Structural Characterization of a Homochiral Secondary Phosphine-Borane Complex. Inorganic chemistry, 35(13), 3874-3877. https://doi.org/10.1021/ic951494h
Bader, Armin, et al. "First Resolution of a Free Secondary Phosphine Chiral at Phosphorus and Stereospecific Formation and Structural Characterization of a Homochiral Secondary Phosphine-Borane Complex." Inorganic chemistry vol. 35,13 (1996): 3874-3877. doi: https://doi.org/10.1021/ic951494h
Bader A, Pabel M, Willis AC, Wild SB. First Resolution of a Free Secondary Phosphine Chiral at Phosphorus and Stereospecific Formation and Structural Characterization of a Homochiral Secondary Phosphine-Borane Complex. Inorg Chem. 1996 Jun 19;35(13):3874-3877. doi: 10.1021/ic951494h. PMID: 11666576.
Copy Download .nbib Format: NLM
Share it on

Inorg Chem. 1996 Jun 19;35(13):3874-3877. doi: 10.1021/ic951494h.

First Resolution of a Free Secondary Phosphine Chiral at Phosphorus and Stereospecific Formation and Structural Characterization of a Homochiral Secondary Phosphine-Borane Complex.

Inorganic chemistry

Armin Bader, Michael Pabel, Anthony C. Willis, S. Bruce Wild

Affiliations

  1. Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, Australian Capital Territory 0200, Australia.

PMID: 11666576 DOI: 10.1021/ic951494h

Abstract

The R(P) diastereomer of (-)-menthylmesitylphosphine, (R(P))-1, has been isolated with high configurational purity at phosphorus by fractional crystallization of an (R(P))-1/(S(P))-1 = 43/57 mixture from acetonitrile containing a trace of sodium acetylacetonate as a proton scavenger or by deboranation of the corresponding borane complex (S(P))-2 with diethylamine, thereby effecting the first resolution of a secondary phosphine chiral at phosphorus. The crystal and molecular structure of (S(P))-2 has been determined. The ready isolation of (S(P))-2 of 97% diastereomeric purity in 66% yield from an equilibrium (R(P))-2/(S(P))-2 = 28/72 mixture in n-hexane by second-order asymmetric transformation and its quantitative and stereospecific conversion under mild conditions into (R(P))-1 of similar purity augurs well for the future of the resolved secondary phosphines in stereoselective syntheses.

Publication Types