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Synthesis 2021; 53(15): 2702-2712
DOI: 10.1055/a-1477-4871
DOI: 10.1055/a-1477-4871
paper
Proline-Histidine Dipeptide: A Suitable Template for Generating Ion-Tagged Organocatalysts for the Asymmetric Aldol Reaction
The work was supported by a collaborative project between the Department of Science and Technology (DST), Ministry of Science and Technology, India (Grant No. INT/RFBR/P-170) and the Russian Foundation for Basic Research (Grant No. 14-03-92701), research grant from the Science and Engineering Research Board (SERB), India (Grant No. EMR/2017/ 005350), a research grant from the Council of Scientific and Industrial Research (CSIR), India (Grant No. 02(0316)/17/EMR-II), and a DST-Fund for Improvement of S&T Infrastructure in Universities and Higher Educational Institutions (FIST) research grant to the Department of Chemistry, CURAJ [Grant No. SR/FST/CSI-257/2014 (C)]. H.I. and M.B. thank the University Grants Commission (UGC), India, and K.K. thanks CSIR, India, for research fellowships. S.E. thanks the Central University of Rajasthan for support.
Abstract
Proline-histidine dipeptide laid the foundation for the construction of three new ion-tagged organocatalysts, utilising the imidazole moiety of histidine for generating the quaternary species. A brief comparative investigation of the catalysts in the enamine-mediated direct asymmetric aldol reaction brought out their contrasting features, particularly under aqueous conditions. The best among them was also utilised in preparing some derivatives and effecting a desymmetrisation.
Key words
dipeptide - ion tag - proline - histidine - asymmetric catalysis - aldol reaction - aqueous reactionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1477-4871.
- Supporting Information
Publication History
Received: 12 November 2020
Accepted after revision: 08 April 2021
Accepted Manuscript online:
08 April 2021
Article published online:
18 May 2021
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