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Synlett 2020; 31(20): 2013-2017
DOI: 10.1055/s-0040-1707302
DOI: 10.1055/s-0040-1707302
letter
Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts
This work was supported in part by a Grant-in-Aid for Scientific Research (C) (No. 15K05123) from MEXT, the Naito Foundation, and the Okayama Foundation for Science and Technology.


Abstract
An enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C 1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.
Key words
nitrocoumarins - Diels–Alder reaction - asymmetric catalysis - organocatalysis - amino alcohols - Danishefsky’s dieneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707302.
- Supporting Information
Publication History
Received: 06 August 2020
Accepted after revision: 02 September 2020
Article published online:
07 October 2020
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