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Literature DB >> 21214182

Enantioselective alkynylation of aldehydes with 1-haloalkynes catalyzed by tethered bis(8-quinolinato) chromium complex.

Abstract

The first example of Cr-catalyzed asymmetric alkynylation of aldehydes with 1-iodo- and 1-bromoalkynes was developed. The use of tethered bis(8-quinolinato) chromium catalyst (3 mol %) allowed preparation of enantioenriched propargyl alcohols with good yields and enantioselectivities up to 92% ee. 1-Bromoalkynes can be activated by the introduction of a cobalt porphine co-catalyst, which enables shorter reaction times without any loss of enantiocontrol.

Entities: Chemical

Year: 2011 PMID： 21214182 DOI： 10.1021/ja1102822

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

8 in total

1. Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

Authors: Prantik Maity; Harathi D Srinivas; Mary P Watson
Journal: J Am Chem Soc Date: 2011-10-11 Impact factor: 15.419

2. Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

Authors: Jiajing Tan; Cheol-Hong Cheon; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2012-07-23 Impact factor: 15.336

3. Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents.

Authors: Jennifer A Dabrowski; Fang Gao; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2011-03-08 Impact factor: 15.419

4. Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes.

Authors: Youzhi Li; Daya Huang; Ju Huang; Yan Liu; Keiji Maruoka
Journal: J Vis Exp Date: 2018-09-12 Impact factor: 1.355

Enantioselective alkynylation of aldehydes with 1-haloalkynes catalyzed by tethered bis(8-quinolinato) chromium complex.

1. Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

2. Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

3. Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents.

4. Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes.

5. Design, synthesis, and evaluation of curcumin-derived arylheptanoids for glioblastoma and neuroblastoma cytotoxicity.

6. Ten years of research in Chicago.

7. Efficient synthesis of 1-iodoalkynes via Al₂O₃ mediated reaction of terminal alkynes and N-iodosuccinimide.

8. A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes.