Itaru Sato

Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis

Enantiomerically enriched pyrimidyl alkanol with either S or R configuration was obtained stochastically from the reaction between pyrimidine-5-carbaldehyde and diisopropylzinc without adding chiral substances in conjunction with subsequent asymmetric autocatalysis, leading to amplification of the enantiomeric excess.

Relationship between the time, yield, and enantiomeric excess of asymmetric autocatalysis of chiral 2-alkynyl-5-pyrimidyl alkanol with amplification of enantiomeric excess

Experimental and kinetic analysis of asymmetric autocatalysis with amplification of ee in the enantioselective addition of diisopropylzinc to 2-alkynylpyrimidine-5-carbaldehyde using chiral 2-alkynyl-5-pyrimidyl alkanol with low ees are described.

Highly enantioselective synthesis of organic compound using right- and left-handed helical silica

Abstract Highly enantiomerically enriched (up to 96–97% ee) 5-pyrimidyl alkanol was obtained by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in the presence of the artificially designed chiral inorganic material, right- and left-handed helical silica.

Evidence of asymmetric autocatalysis in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde using chiral pyrimidyl alkanol

Abstract Kinetic analysis of the relationship between the reaction time and the yields of the product in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde using chiral pyrimidyl alkanol proves that the reaction is autocatalytic.

Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes

Abstract Chiral dendrimers with three or six β-amino alcohols on hyperbranched hydrocarbon chain-ends were synthesized. These macromolecules can act as chiral catalysts for the enantioselective addition of dialkylzincs to aldehydes. The corresponding secondary alcohols are obtained in high enantiomeric excess (up to 86% e.e.).

Highly enantioselective addition of diethylzinc to N-diphenylphosphinylimines using dendritic chiral ligands with hydrocarbon backbones

Abstract Chiral dendrimers bearing three or six chiral β-amino alcohols on the hyperbranched hydrocarbon chain-ends act as efficient chiral ligands for the enantioselective addition of diethylzinc to N -diphenylphosphinylimines to afford enantiomerically enriched N -diphenylphosphinylamines with up to 94% e.e.

Highly enantioselective addition of dialkylzincs to aldehydes using dendritic chiral catalysts with flexible carbosilane backbones

Abstract Chiral dendrimers bearing four or twelve chiral β-amino alcohols on the hyperbranched flexible carbosilane chain-ends act as efficient chiral catalysts for the enantioselective addition of dialkylzinc to aldehydes to afford enantiomerically enriched sec -alcohols with up to 93% e.e.

Highly Enantioselective Asymmetric Autocatalysis of Pyrimidin-5-yl Alkanol Induced by Chiral 1,3-Disubstituted Hydrocarbon Allenes

1,3-Disubstituted chiral allenes without any heteroatoms act as chiral initiators in the addition of (i-Pr)2Zn to pyrimidine-5-carbaldehyde to afford, in combination with the subsequent asymmetric autocatalysis, chiral pyrimidin-5-yl alkanols with up to 98% ee. The absolute configuration of the pyrimidin-5-yl alkanol formed depend on that of the chiral allene.

Asymmetric autocatalysis of 5-carbamoyl-3-pyridyl alkanols with amplification of enantiomeric excess

Abstract 5-Carbamoyl-3-pyridyl alkanols with low e.e. act as asymmetric autocatalysts in the consecutive asymmetric autocatalytic addition of diisopropylzinc to 5-carbamoyl-3-pyridinecarbaldehydes. The e.e. of pyridyl alkanol amplified up to 88% e.e. without the need for any other chiral auxiliary.

Self‐Replication and Amplification of Enantiomeric Excess of Chiral Multifunctionalized Large Molecules by Asymmetric Autocatalysis

Self-replication of large chiral molecular architectures is one of the great challenges and interests in synthetic, systems, and prebiotic chemistry. Described herein is a new chemical system in which large chiral multifunctionalized molecules possess asymmetric autocatalytic self-replicating and self-improving abilities, that is, improvement of their enantioenrichment in addition to the diastereomeric ratio. The large chiral multifunctionalized molecules catalyze the production of themselves with the same structure, including the chirality of newly formed asymmetric carbon atoms, in the reaction of the corresponding achiral aldehydes and reagent. The chirality of the large multifunctionalized molecules controlled the enantioselectivity of the reaction in a highly selective manner to construct multiple asymmetric stereogenic centers in a single reaction.