Intramolecular reductive amination strategy to the synthesis of ( R)- N-Boc-2-hydroxymethylmorpholine, N-(3,4-dichlorobenzyl)( R)-2-hydroxymethylmorpholine, and ( R)-2-benzylmorpholine

A concise high yielding enantioselective synthesis of ( R)- N-Boc-2-hydroxymethylmorpholine, N-(3,4-dichlorobenzyl)( R)-2-hydroxymethylmorpholine, and ( R)-benzylmorpholine has been achieved by employing proline-catalyzed asymmetric α-aminooxylation of aldehyde and palladium-catalyzed intramolecular...

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Bibliographic Details
Published in:Tetrahedron 2010-03, Vol.66 (11), p.2010-2014
Main Authors: Sawant, Rajiv T., Waghmode, Suresh B.
Format: Article
Language:English
Subjects:
Asymmetric α-aminooxylation
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Morpholines
Organic chemistry
Pharmacologically active
Preparations and properties
Proline
Reductive amination
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Summary:A concise high yielding enantioselective synthesis of ( R)- N-Boc-2-hydroxymethylmorpholine, N-(3,4-dichlorobenzyl)( R)-2-hydroxymethylmorpholine, and ( R)-benzylmorpholine has been achieved by employing proline-catalyzed asymmetric α-aminooxylation of aldehyde and palladium-catalyzed intramolecular reductive amination of azido aldehyde as the key steps. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.01.047