On the origins of kinetic resolution of cyclohexane-1,2-diols through stereoselective acylation by chiral tetrapeptides

Organic Letters

Volumn 11, Issue 15, 2009, Pages 3242-3245

  Shinisha, C B ^a   Sunoj, Raghavan B ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,2-CYCLOHEXANEDIOL; CYCLOHEXANE 1,2 DIOL; CYCLOHEXANOL DERIVATIVE; OLIGOPEPTIDE;

ACYLATION; ARTICLE; CHEMISTRY; KINETICS; STEREOISOMERISM;

ACYLATION; CYCLOHEXANOLS; KINETICS; OLIGOPEPTIDES; STEREOISOMERISM;

EID: 68149141348     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9011822     Document Type: Article

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31. In the nomenclature used for inclusion complexes and transition states, the subscripts a (axial) or e (equatorial) refer to the position of -OAc and -OH in the product and notations α and β refer to the orientations of -OH in the diol to which the acetyl group is transferred.
32. A comprehensive comparison of such deviations is given in Figure S3 in Supporting Information.
33. Figure S4 showing these interactions is given in Supporting Information.
34. A comparison of these transition state features is given in Figure S2 of Supporting Information.
35. The optimized geometries of lower-energy transition states for the acylation reaction of cis-cyclohexane-1,2-diol are given in Figure S1 of Supporting Information.