0000000001303680
AUTHOR
Shinobu Takizawa
ChemInform Abstract: o-(Hydroxyalkyl)phenyl P-Chirogenic Phosphines as Functional Chiral Lewis Bases.
The stereoselective synthesis of P-chirogenic phosphines bearing an o-hydroxyalkyl chain is described.
o-(Hydroxyalkyl)phenyl P-Chirogenic Phosphines as Functional Chiral Lewis Bases
The stereoselective synthesis of P-chirogenic phosphines bearing an o-hydroxyalkyl chelating arm is described. The synthesis is based either on the hydroxyalkylation of P-chirogenic o-bromophenylphosphines (borane) or on their carbonatation and then reduction. The hydroxyalkylation with benzaldehyde or pivalaldehyde affords a mixture of epimers which are isolated by chromatography and characterized by their X-ray structures. Preliminary assays of free P-chirogenic o-(hydroxyalkyl)phenyl phosphines, as new functional Lewis bases in catalyzed asymmetric aza-MBH reaction, lead to β-aminoester derivatives with ee values up to 74%.
P-chirogenic organocatalysts: application to the aza-Morita–Baylis–Hillman (aza-MBH) reaction of ketimines
The P-chirogenic organocatalysts were found to promote the enantioselective aza-Morita-Baylis-Hillman reaction of ketimines derived from acyclic α-keto esters. In the P-chirogenic organocatalyzed aza-MBH reactions, α,α-disubstituted α-amino acid derivatives were obtained in high yields with high enantioselectivities (up to 97% ee).
CCDC 945143: Experimental Crystal Structure Determination
Related Article: Shinobu Takizawa, Emmanuelle Rémond, Fernando Arteaga Arteaga, Yasushi Yoshida, Vellaisamy Sridharan, Jérôme Bayardon, Sylvain Jugé, Hiroaki Sasai|2013|Chem.Commun.|49|8392|doi:10.1039/C3CC44549F
CCDC 937024: Experimental Crystal Structure Determination
Related Article: Emmanuelle Rémond, Jérôme Bayardon, Shinobu Takizawa, Yoann Rousselin, Hiroaki Sasai, and Sylvain Jugé|2013|Org.Lett.|15|1870|doi:10.1021/ol400515e
CCDC 937026: Experimental Crystal Structure Determination
Related Article: Emmanuelle Rémond, Jérôme Bayardon, Shinobu Takizawa, Yoann Rousselin, Hiroaki Sasai, and Sylvain Jugé|2013|Org.Lett.|15|1870|doi:10.1021/ol400515e
CCDC 937025: Experimental Crystal Structure Determination
Related Article: Emmanuelle Rémond, Jérôme Bayardon, Shinobu Takizawa, Yoann Rousselin, Hiroaki Sasai, and Sylvain Jugé|2013|Org.Lett.|15|1870|doi:10.1021/ol400515e
CCDC 937023: Experimental Crystal Structure Determination
Related Article: Emmanuelle Rémond, Jérôme Bayardon, Shinobu Takizawa, Yoann Rousselin, Hiroaki Sasai, and Sylvain Jugé|2013|Org.Lett.|15|1870|doi:10.1021/ol400515e