Disclosed are methods for preparing deuterated analogs of D-serine and compounds useful for preparing deuterated analogs of D-serine.

Disclosed are methods for preparing deuterated analogs of D-serine and compounds useful for preparing deuterated analogs of D-serine.

Objects of the present invention are to provide an industrially applicable method for producing an optically active -amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ,-disubstituted -amino acid, and to provide an intermediate useful for the above production methods of an optically active -amino acid and an optically active ,-disubstituted -amino acid. The present invention provides a production method of an optically active -amino acid or a salt thereof, the production method comprising introducing a substituent into the carbon in the -amino acid moiety of a metal complex represented by the following Formula (1): ##STR00001##
by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure -amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Objects of the present invention are to provide an industrially applicable method for producing an optically active -amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ,-disubstituted -amino acid, and to provide an intermediate useful for the above production methods of an optically active -amino acid and an optically active ,-disubstituted -amino acid. The present invention provides a production method of an optically active -amino acid or a salt thereof, the production method comprising introducing a substituent into the carbon in the -amino acid moiety of a metal complex represented by the following Formula (1): ##STR00001##
by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure -amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Objects of the present invention are to provide an industrially applicable method for producing an optically active -amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ,-disubstituted -amino acid, and to provide an intermediate useful for the above production methods of an optically active -amino acid and an optically active ,-disubstituted -amino acid. The present invention provides a production method of an optically active -amino acid or a salt thereof, the production method comprising introducing a substituent into the carbon in the -amino acid moiety of a metal complex represented by the following Formula (1): ##STR00001##
by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure -amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

An object of the present invention is to provide a method for producing an optically active amino acid in high yield and in a highly enantioselective manner, which method has fewer restrictions on the material that can be used as the substrate, and to provide, among others, a compound useful as a chiral auxiliary for the method. The present invention provides an N-(2-acylaryl)-2-[5,7-dihydro-6H-dibenzo[c,e]azepin-6-yl]acetamide compound represented by Formula (1): ##STR00001##
or a salt thereof, or a metal complex represented, by Formula (3): ##STR00002##

An object of the present invention is to provide a method for producing an optically active amino acid in high yield and in a highly enantioselective manner, which method has fewer restrictions on the material that can be used as the substrate, and to provide, among others, a compound useful as a chiral auxiliary for the method. The present invention provides an N-(2-acylaryl)-2-[5,7-dihydro-6H-dibenzo[c,e]azepin-6-yl]acetamide compound represented by Formula (1): ##STR00001##
or a salt thereof, or a metal complex represented, by Formula (3): ##STR00002##

Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.

Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.

The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafine, Naftifine 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral -aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of -aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-1-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials. A novel chiral copper-BINAM nitrosoarene complex is also set forth.