Method for synthesizing novel chiral ligand, metal chelate, a variety of non-natural amino acids, maraviroc and key intermediate thereof

A novel resolution method for an alpha amino acid, an alpha substituted beta amino acid and a beta substituted beta amino acid comprising the step of hydrolyzing a compound of formula VI to obtain the alpha amino acid, the alpha substituted beta amino acid and the beta substituted beta amino acid of formula VII,

• wherein n is an integer from 1 to 4, m is an integer from 0 to 1;
• R is selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl and unsubstituted or substituted phenyl, wherein the substituted phenyl means that the phenyl has 1-5 substituents, and each substituent is independently selected from the group consisting of amino, halogen, hydroxyl, C1-C4 alkyl and C1-C4 haloalkyl;
• R1 is selected from the group consisting of H, C1-C4 alkyl, C1-C4 haloalkyl and unsubstituted or substituted phenyl, wherein the substituted phenyl means that the phenyl has 1-5 substituents, and each substituent is independently selected from the group consisting of amino, halogen, hydroxyl, C1-C4 alkyl and C1-C4 haloalkyl;
• R2 is selected from the group consisting of H, halogen, amino, hydroxyl, C1-C4 alkyl and C1-C4 haloalkyl;
• R3 is selected from the group consisting of H, C1-C4 alkyl, C1-C4 haloalkyl, unsubstituted or substituted phenyl and —(C1-C4 alkylene)-(unsubstituted or substituted phenyl);
• wherein the substituted phenyl means that the phenyl has 1-5 substituents, and each substituent is independently selected from the group consisting of amino, halogen, hydroxyl, C1-C4 alkyl and C1-C4 haloalkyl;
• R4 is selected from the group consisting of H, unsubstituted or substituted C6-C10 aryl, unsubstituted or substituted C3-C6 heteroaryl and unsubstituted or substituted C3-C6 cycloalkyl, wherein the “substituted” means that there are 1-5 substituents, and each substituent is independently selected from the group consisting of amino, halogen, hydroxyl, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 haloalkyl;
• R5 is selected from the group consisting of H, unsubstituted or substituted C6-C10 aryl, unsubstituted or substituted C3-C6 heteroaryl and unsubstituted or substituted C3-C6 cycloalkyl, wherein the “substituted” means that there are 1-5 substituents, and each substituent is independently selected from the group consisting of amino, halogen, hydroxyl, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 haloalkyl.