ChemInform Abstract: Kinetic Resolution of Amino Alcohol Derivatives with a Chiral Nucleophilic Catalyst: Access to Enantiopure Cyclic cis‐Amino Alcohols.

Abstract

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Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases

“… A representative example is ( S )-2-amino-3-methyl-1-butanol ( l -valinol), which is used as a key intermediate in the synthesis of the HIV-1 integrase inhibitor Elvitegravir. , Chiral amino alcohols also serve as important chiral auxiliaries or ligands in various asymmetric syntheses . From a chemical synthesis perspective, chiral vicinal amino alcohols can be accessed via reduction of amino acids or α-amino carbonyl compounds, cross-coupling of imines with carbonyl compounds, opening of epoxides by nitrogen nucleophiles, aminohydroxylation of alkenes, and kinetic resolution of racemates . However, several drawbacks remain, including harsh reaction conditions, the use of expensive transition metal catalysts, and insufficient regio- and enantioselectivity.…”

Strategies for Accessing cis-1-Amino-2-Indanol

“…Another general strategy for β-amino-alcohol resolution is to perform a kinetic resolution via enantioselective acylation of the alcohol in the presence of a chiral nucleophilic catalyst. Kawabata’s group implemented this approach in cis -1-amino-2-indanol with a chiral aminopyridine as a catalyst ( Scheme 31 ) [ 94 ]. After a screening, 4-(dimethylamino)benzamide was determined to be the best protecting group for the amine function.…”