Synthesis 2016; 48(20): 3449-3458
DOI: 10.1055/s-0035-1562475
short review
© Georg Thieme Verlag Stuttgart · New York

Non-Classical C–H···X Hydrogen Bonding and Its Role in Asymmetric Organocatalysis

Manjaly J. Ajitha
Division of Physical Sciences & Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia   eMail: hkw@kaust.edu.sa
,
Kuo-Wei Huang*
Division of Physical Sciences & Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia   eMail: hkw@kaust.edu.sa
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Publikationsverlauf

Received: 11. Mai 2016

Accepted after revision: 19. Juni 2016

Publikationsdatum:
17. August 2016 (online)


Abstract

Non-classical hydrogen bonds (NCHBs) have attracted significant interest in the past decade particularly because of their important role in asymmetric catalytic systems. These weak interactions (<4 kcal/mol) offer much flexibility in the preorganization of molecular entities required to achieve high enantioselectivity. Herein, we review some recent important organocatalytic asymmetric reactions where a NCHB serves as a critical factor in determining the stereoselectivity.

1 Introduction

2 Hydrogen Bonds (HBs) and Non-Classical Hydrogen Bonds (NCHBs)

3 Early Developments in NCHBs

4 Selected Examples of NCHBs in Organic Transformations

5 Recent Examples of NCHBs in Enantioselective Reactions

6 Conclusions and Outlook

 
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