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. 2021 Dec 23;27(72):18033-18038.
doi: 10.1002/chem.202103254. Epub 2021 Nov 8.

Parts-per-Million-Level, Catalytic [3+2]-Annulations for the Asymmetric Synthesis of Methanobenzo[7]annulenes

Guguloth Thirupathi  1 , Etikala Ashok  1 , A Suresh Kumar  1 , Dhevalapally B Ramachary  1
Affiliations

Parts-per-Million-Level, Catalytic [3+2]-Annulations for the Asymmetric Synthesis of Methanobenzo[7]annulenes

Guguloth Thirupathi et al. Chemistry. .

Abstract

3-Alkyl-lawsones selectively reacted with α-alkyl-nitroethylenes under 500 parts-per-million (ppm) quinine-NH-thiourea-catalysis to furnish the chiral methanobenzo[7]annulenes in up to >99 % ee with >20 : 1 dr and TON up to 1820 through tandem Michael/Henry [3+2]-annulations. These asymmetric ppm-level, catalytic tandem [3+2]-annulations would be highly inspirational for the design of many more ppm-level organocatalytic reactions, and at the same time these final molecules are basic skeletons of antibiotics.

Keywords: annulations; antibiotics; asymmetric catalysis; lawsone; ppm-level catalysis.

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References

    1. None
    1. H. B. Park, T. N. Goddard, J. Oh, J. Patel, Z. Wei, C. E. Perez, B. Q. Mercado, R. Wang, T. P. Wyche, G. Piizzi, R. A. Flavell, J. M. Crawford, Angew. Chem. Int. Ed. 2020, 59, 7871-7880;
    1. Angew. Chem. 2020, 132, 7945-7954;
    1. F. Rudroff, M. D. Mihovilovic, H. Gröger, R. Snajdrova, H. Iding, U. T. Bornscheuer, Nat. Catal. 2018, 1, 12-22;
    1. J. Shi, Y. Wu, S. Zhang, Y. Tian, D. Yang, Z. Jiang, Chem. Soc. Rev. 2018, 47, 4295-4313;

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