Jik Chin Group – Professor Product Portal

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Professor Jik Chin

The Chin group is interested in computational and experimental approaches to understanding stereoselective recognition and catalysis. Their studies in weak forces (H-bonding, electronic and steric effects) has led to a highly efficient method for making limitless varieties of chiral vicinal diamines from the 'mother diamine' that are useful for developing stereoselective organocatalysts or transition metal-based catalysts as well as for developing drugs (Acc Chem Res (2012) p1345). The 'mother diamine' is also useful for making binol, monophos and binap analogs.

The Chin group is also interested in using reversible covalent bonds for stereoselective recognition and L to D conversion of natural and non-natural amino acids (EJOC (2012) p229).

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Soon Mog SM So et. al
Accounts of Chemical Research, 45(8), 1345-1355 (2012)
Chiral diamines are important building blocks for constructing stereoselective catalysts, including transition metal based catalysts and organocatalysts that facilitate oxidation, reduction, hydrolysis, and C-C bond forming reactions. These molecules...Read More
Soon Ho Kwon et. al
Organic Letters, 14(14), 3664-3667 (2012)
An efficient synthetic method was developed for the construction of enantiomerically pure trans-3-arylpiperazine-2-carboxylic acid derivatives using diaza-Cope rearrangement (DCR) as a key step starting from (R,R)/(S,S)-1,2-bis(2-hyd...Read More
Hyunwoo Kim and Jik Chin
Organic Letters, 11(22), 5258-5260 (2009)
Diaza-Cope rearrangement is used to make a variety of alpha-substituted syn-alpha,beta-diamino acids. The rearrangement takes place with complete transfer of stereochemical integrity (>97% de and >98% ee) giving only one of four possible stereoisomer...Read More
Hyunwoo H Kim et. al
Organic Letters, 11(1), 157-160 (2009)
Addition of isobutyraldehyde to 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (mother diamine) cleanly gives a stable, fused imidazolidine-dihydro-1,3-oxazine ring complex. However, vigorous heating of the fused ring complex gives the diaza-Cope rearran...Read More
Hyunwoo H Kim et. al
Journal of the American Chemical Society, 130(36), 12184-12191 (2008)
Sixteen diphenylethylenediamine analogues including those with electron donating, electron withdrawing, and sterically bulky substituents have been prepared in good overall yields (70-90%) and in enantiomerically pure form (>99% ee) by diaza-Cope rea...Read More
Hyunwoo Kim et. al
Angewandte Chemie (International Edition), 47(45), 8678-8681 (2008)