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To investigate the recovery of amino alcohols as chiral auxiliaries, optically active p-benzyloxyphenylglycinol and its corresponding oxazolidine of 1-naphthylcarboxaldehyde were prepared. Grignard additions to the oxazolidine followed by electrophilic quench and acidic hydrolysis afforded an aldehyde(compound 8)(later it was reduced to an alcohol, compound 9) in an excellent enantiomeric excess and a good recovery of the chiral amino alcohol. This research provides a model study of chiral amino alcohols in solid phase asymmetric synthesis.
To investigate the recovery of amino alcohols as chiral auxiliaries, optically active p-benzyloxyphenylglycinol and its corresponding oxazolidine of 1-naphthylcarboxaldehyde were prepared. Grignard additions to the oxazolidine followed by electrophilic quench and acidic hydrolysis afforded an aldehyde (compound 8) (later it was reduced to an alcohol, compound 9) in an excellent enantiomeric excess and a good recovery of the chiral amino alcohol. This research provides a model study of chiral amino alcohols in solid phase asymmetric synthesis.