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Literature DB >> 22422718

Catalytic enantiospecific [3+2] annulation of aminocyclopropanes with ketones.

Fides Benfatti¹, Florian de Nanteuil, Jérôme Waser.

Abstract

An almost familiar ring: The first enantiospecific [3+2] annulation of donor-acceptor aminocyclopropanes with ketones is reported (see scheme; Phth=phthaloyl). The reaction is catalysed by tin(IV) chloride (5 mol %) at -78 °C and gives aminotetrahydrofurans bearing a quaternary C5 atom in high yield, diastereoselectivity and enantiospecificity (see scheme).

Entities: Chemical Species

Year: 2012 PMID： 22422718 DOI： 10.1002/chem.201103971

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

12 in total

1. Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes.

Authors: Todd K Hyster; Tomislav Rovis
Journal: Synlett Date: 2013 Impact factor: 2.454

2. Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

Authors: Grzegorz Mlostoń; Mateusz Kowalczyk; André U Augustin; Peter G Jones; Daniel B Werz
Journal: European J Org Chem Date: 2021-08-25

3. One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

Authors: Qiong-Jie Liu; Wen-Guang Yan; Lijia Wang; X Peter Zhang; Yong Tang
Journal: Org Lett Date: 2015-08-07 Impact factor: 6.005

4. Asymmetric cyclopropanation of chalcones using chiral phase-transfer catalysts.

Authors: Richard Herchl; Mario Waser
Journal: Tetrahedron Lett Date: 2013-05-15 Impact factor: 2.415

5. Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals.

Authors: Haipan Zhu; Peile Du; Jianjun Li; Ziyang Liao; Guohua Liu; Hao Li; Wei Wang
Journal: Beilstein J Org Chem Date: 2016-06-29 Impact factor: 2.883

Catalytic enantiospecific [3+2] annulation of aminocyclopropanes with ketones.

1. Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes.

2. Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

3. One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

4. Asymmetric cyclopropanation of chalcones using chiral phase-transfer catalysts.

5. Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals.

6. Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes.

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

8. Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles.

Review 9. Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.

10. Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.