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Literature DB >> 28504482

Asymmetric Copper-Catalyzed Carbomagnesiation of Cyclopropenes.

Longyang Dian¹, Daniel S Müller¹, Ilan Marek¹.

Abstract

The highly diastereo- and enantioselective formation of polysubstituted cyclopropanes was easily achieved through the asymmetric copper-catalyzed carbomagnesiation reaction of nonfunctionalized cyclopropene derivatives. The carbometalated species generated in situ readily undergo C-C and C-X bond-forming reactions with various electrophiles with complete retention of configuration.

Entities: Chemical

Keywords: asymmetric catalysis; carbometalation; configurational stability; cyclopropanes; cyclopropenes

Year: 2017 PMID： 28504482 DOI： 10.1002/anie.201701094

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

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Cited

18 in total

1. Directed nucleophilic addition of phenoxides to cyclopropenes.

Authors: Pavel Yamanushkin; Michael Lu-Diaz; Andrew Edwards; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal: Org Biomol Chem Date: 2017-10-04 Impact factor: 3.876

2. Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates.

Authors: Vladimir A Maslivetc; Liliya V Frolova; Snezna Rogelj; Anna A Maslivetc; Marina Rubina; Michael Rubin
Journal: J Org Chem Date: 2018-10-30 Impact factor: 4.354

Asymmetric Copper-Catalyzed Carbomagnesiation of Cyclopropenes.

1. Directed nucleophilic addition of phenoxides to cyclopropenes.

2. Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates.

3. Cobalt-Catalyzed Reductive Dimethylcyclopropanation of 1,3-Dienes.

4. Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

5. Efficient and stereodivergent synthesis of unsaturated acyclic fragments bearing contiguous stereogenic elements.

6. Diastereo- and enantioselective copper catalyzed hydroallylation of disubstituted cyclopropenes.

Review 7. Toward ideal carbon dioxide functionalization.

8. Diastereo- and enantioselective preparation of cyclopropanol derivatives.

9. Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.

Review 10. Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres.