Sterically encumbered chiral amino alcohols for the titanium catalyzed asymmetric alkylation of benzaldehyde

Sterically encumbered chiral l-amino alcohols with secondary amines and tertiary alcohols catalyze the enantioselective alkylation of benzaldehyde with diethyl zinc. Using 2mol% of amino alcohol catalyst predominantly gave (R)-1-phenylpropanol with enantiomeric excesses of up to 61%. Using the in si...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2012-04, Vol.23 (6-7), p.501-507
Main Authors: Jones, Casey M., Li, Hanhan, Hickman, Amanda J., Hughs, Lauren D., Sobelman, Samuel J., Johnson, Adam R.
Format: Article
Language:English
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Summary:Sterically encumbered chiral l-amino alcohols with secondary amines and tertiary alcohols catalyze the enantioselective alkylation of benzaldehyde with diethyl zinc. Using 2mol% of amino alcohol catalyst predominantly gave (R)-1-phenylpropanol with enantiomeric excesses of up to 61%. Using the in situ prepared titanium complex at 2mol% as catalyst also favored the (R)-enantiomer with enantiomeric excesses of up to 73%. In almost all cases, the addition catalyzed by the titanium complex exhibited higher enantioselectivity than that of the amino alcohol ligand alone.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2012.03.016