Abstract
A new type of N,P chiral ligand, binaphthyl amino phosphine 1 was synthesized through a simple and practical resolution of racemic 2-amino-2'- hydroxy-1,1'-binaphthyl by molecular complexation with 0.5 equivalents of N- benzylcinchonidium chloride in the solid state. The present procedure represents the first example of the optical resolution of amino alcohol with the use of a chiral ammonium salt as a resolving reagent. The resolution mechanism is discussed in terms of molecular recognition in solid state. The chlorine anion in N-benzylcinchonidium chloride provides the bridging link between two amino alcohol molecules [(+)-2] and the cinchonoid cation located in between, by hydrogen bonding with the surrounding moieties.
Original language | English |
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Pages (from-to) | 1734-1737 |
Number of pages | 4 |
Journal | Chemistry - A European Journal |
Volume | 5 |
Issue number | 6 |
DOIs | |
Publication status | Published - 1999 |
Externally published | Yes |
Keywords
- Amino alcohols
- Biaryls
- Molecular recognition
- N,P ligands
- Optical resolution
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry