Literature DB >> 16305204

Preorganization in highly enantioselective diaza-Cope rearrangement reaction.

Hae-Jo Kim1, Hyunwoo Kim, Gamil Alhakimi, Eui June Jeong, Nirusha Thavarajah, Lisa Studnicki, Alicja Koprianiuk, Alan J Lough, Junghun Suh, Jik Chin.   

Abstract

Crystal structure and activation entropy data indicate that H-bond directed diaza-Cope rearrangement of chiral diimines takes place with a high degree of preorganization. CD spectroscopy and HPLC data show that there is inversion of stereochemistry for the reaction with excellent enantioselectivity.

Entities:  

Year:  2005        PMID: 16305204     DOI: 10.1021/ja055776k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  3 in total

1.  High-throughput screening of identity, enantiomeric excess, and concentration using MLCT transitions in CD spectroscopy.

Authors:  Sonia Nieto; Vincent M Lynch; Eric V Anslyn; Hyunwoo Kim; Jik Chin
Journal:  J Am Chem Soc       Date:  2008-06-24       Impact factor: 15.419

2.  Rapid enantiomeric excess and concentration determination using simple racemic metal complexes.

Authors:  Sonia Nieto; Vincent M Lynch; Eric V Anslyn; Hyunwoo Kim; Jik Chin
Journal:  Org Lett       Date:  2008-10-22       Impact factor: 6.005

3.  Tandem diaza-Cope rearrangement polymerization: turning intramolecular reaction into powerful polymerization to give enantiopure materials for Zn2+ sensors.

Authors:  Soon-Hyeok Hwang; Tae-Lim Choi
Journal:  Chem Sci       Date:  2020-12-08       Impact factor: 9.825

  3 in total

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