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On the Origins of Kinetic Resolution of Cyclohexane-1,2-diols Through Stereoselective Acylation by Chiral Tetrapeptides

DSpace at IIT Bombay

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Title On the Origins of Kinetic Resolution of Cyclohexane-1,2-diols Through Stereoselective Acylation by Chiral Tetrapeptides
 
Creator SHINISHA, CB
SUNOJ, RB
 
Subject peptide-based catalysts
asymmetric catalysis
alcohols
acids
 
Description The relative energies of cyclohexane-1,2-diols and chiral tetrapeptide (2 (Boc) or 3 (Moc)) complexes calculated using DFT indicate a thermodynamic preference for chiral recognition toward (1R,2R)(e,e)-alpha isomer. The barrier for stereoselective acyl transfer is identified as lower for trans-(1R,2R)-cyclohexane-1,2-diol, leading to the kinetic resolution (KR) of trans-(1S,2S)-cyclohexane-1,2-diol. The prediction is in concert with the reported experiments for trans-diols, while that for hitherto unknown cis-diol demands experimental verification. It is proposed that desymmetrization would enable the resolution of cis-(1R,2S)-2-hydroxycyclohexyl acetate.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T14:20:44Z
2011-12-26T12:48:26Z
2011-12-27T05:38:03Z
2011-07-14T14:20:44Z
2011-12-26T12:48:26Z
2011-12-27T05:38:03Z
2009
 
Type Article
 
Identifier ORGANIC LETTERS, 11(15), 3242-3245
1523-7060
http://dx.doi.org/10.1021/ol9011822
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3980
http://hdl.handle.net/10054/3980
 
Language en