Hydroxyproline-derived pseudoenantiomeric [2.2.1] bicyclic phosphines: asymmetric synthesis of (+)- and (-)-pyrrolines.

Journal of the American Chemical Society (2014-08-08)
Christopher E Henry, Qihai Xu, Yi Chiao Fan, Tioga J Martin, Lee Belding, Travis Dudding, Ohyun Kwon
RESUMEN

We have prepared two new diastereoisomeric 2-aza-5-phosphabicyclo[2.2.1]heptanes from naturally occurring trans-4-hydroxy-L-proline in six chemical operations. These syntheses are concise and highly efficient, with straightforward purification. When we used these chiral phosphines as catalysts for reactions of γ-substituted allenoates with imines, we obtained enantiomerically enriched pyrrolines in good yields with excellent enantioselectivities. These two diastereoisomeric phosphines functioned as pseudoenantiomers, providing their chiral pyrrolines with opposite absolute configurations.

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Sigma-Aldrich
Endo-Phenyl Kwon [2.2.1] Bicyclic Phosphine, 95% (HPLC)
Sigma-Aldrich
Endo-4-Methoxyphenyl Kwon [2.2.1] Bicyclic Phosphine
Sigma-Aldrich
Exo-Phenyl Kwon [2.2.1] Bicyclic Phosphine, 95% (HPLC)
Sigma-Aldrich
Endo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
Sigma-Aldrich
Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
Sigma-Aldrich
Exo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
Sigma-Aldrich
Exo-4-anisole Kwon [2.2.1] bicyclic phosphine
Sigma-Aldrich
Endo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

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