Stereospecific Synthesis of gamma,delta-Diamino Esters

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gamma,delta-Diamino acid structural motifs are commonly found in bioactive molecules. We report a one-pot reaction for the synthesis of gamma,delta-diimino esters with two adjacent chiral centers in enantiomerically pure form through diaza-Cope rearrangement reaction of diimines formed from (R,R)-1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (hpen) and alde-hydes. DFT computation provides interesting insights into the stereospecific rearrangement reaction. The crystal structure of a product diimine formed from the reaction of (R,R)-hpen and 2,6-dichlorobenzaldehyde shows that the reaction gives the product diimine in S,S configuration.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2014-02
Language
English
Article Type
Article
Citation

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.4, pp.725 - 730

ISSN
1434-193X
DOI
10.1002/ejoc.201301167
URI
http://hdl.handle.net/10203/189229
Appears in Collection
CH-Journal Papers(저널논문)
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