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Literature DB >> 29461662

Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor-Acceptor meso-Diaminocyclopropanes.

Daniele Perrotta¹, Ming-Ming Wang¹, Jérôme Waser¹.

Abstract

The first Lewis acid catalyzed enantioselective ring-opening desymmetrization of a donor-acceptor meso-diaminocyclopropane is reported. The copper(II)-catalyzed Friedel-Crafts alkylation of indoles and one pyrrole with an unprecedented meso-diaminocyclopropane delivered enantioenriched, diastereomerically pure urea products, which are structurally related to natural and synthetic bioactive compounds. The development of a new ligand through the investigation of an underexplored subclass of bis(oxazoline) ligands was essential for achieving high enantioselectivities.

Entities: Chemical Species

Keywords: BOX ligands; Lewis acids; desymmetrization; donor-acceptor cyclopropanes; ureas

Year: 2018 PMID： 29461662 DOI： 10.1002/anie.201800494

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

8 in total

1. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors: Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal: Chem Rev Date: 2021-05-21 Impact factor: 60.622

2. Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.

Authors: Saki Ichikawa; Xi-Jie Dai; Stephen L Buchwald
Journal: Org Lett Date: 2019-05-17 Impact factor: 6.005

3. New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes.

Authors: Niankai Fu; Lu Song; Jinjian Liu; Yifan Shen; Juno C Siu; Song Lin
Journal: J Am Chem Soc Date: 2019-09-09 Impact factor: 15.419

4. Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

Authors: Xinxin Shao; Kangnan Li; Steven J Malcolmson
Journal: J Am Chem Soc Date: 2018-05-30 Impact factor: 15.419

Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor-Acceptor meso-Diaminocyclopropanes.

1. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

2. Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.

3. New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes.

4. Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

5. A novel type of donor-acceptor cyclopropane with fluorine as the donor: (3 + 2)-cycloadditions with carbonyls.

6. (4+3) Annulation of Donor-Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones.

Review 7. Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.

8. Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor-Acceptor Cyclopropanes.