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Literature DB >> 27373124

Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams.

Masaki Hayashi¹, Shoshana Bachman¹, Satoshi Hashimoto¹, Chad C Eichman^1,2, Brian M Stoltz¹.

Abstract

A new strategy for catalytic enantioselective C-acylation to generate α-quaternary-substituted lactams is reported. Ni-catalyzed three-component coupling of lactam enolates, benzonitriles, and aryl halides produces β-imino lactams that then afford β-keto lactams by acid hydrolysis. Use of a readily available Mandyphos-type ligand and addition of LiBr enable the construction of quaternary stereocenters on α-substituted lactams to form β-keto lactams in up to 94% ee.

Entities: Chemical Disease Gene

Mesh：

Substances：
Lactams
Carbon
Nickel

Year: 2016 PMID： 27373124 PMCID： PMC4963289 DOI： 10.1021/jacs.6b02120

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

33 in total

1. A dual-catalysis approach to the asymmetric Steglich rearrangement and catalytic enantioselective addition of O-acylated azlactones to isoquinolines.

Authors: Chandra Kanta De; Nisha Mittal; Daniel Seidel
Journal: J Am Chem Soc Date: 2011-09-29 Impact factor: 15.419

2. First Catalytic C-Acylation of Enoxysilanes: An Efficient Route to beta-Diketones(1).

Authors: Christophe Le Roux; Stéphanie Mandrou; Jacques Dubac
Journal: J Org Chem Date: 1996-05-31 Impact factor: 4.354

3. Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes: effect of halide on selectivity, oxidation state, and room-temperature reactions.

Authors: Shaozhong Ge; John F Hartwig
Journal: J Am Chem Soc Date: 2011-09-27 Impact factor: 15.419

4. Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile.

Authors: Ara H Mermerian; Gregory C Fu
Journal: J Am Chem Soc Date: 2003-04-09 Impact factor: 15.419

5. Synthesis and catalytic properties of 4-aryl-2,3-dihydro-4H-pyrimido[2,3-b]benzothiazoles for asymmetric acyl or carboxyl group transfer reactions.

Authors: Baby Viswambharan; Tatsuya Okimura; Satoko Suzuki; Sentaro Okamoto
Journal: J Org Chem Date: 2011-07-26 Impact factor: 4.354

6. Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N,N-4-(Dimethylamino)pyridine Derivatives.

Authors: Hiroki Mandai; Takuma Fujiwara; Katsuaki Noda; Kazuki Fujii; Koichi Mitsudo; Toshinobu Korenaga; Seiji Suga
Journal: Org Lett Date: 2015-09-10 Impact factor: 6.005

7. Catalytic enantioselective construction of all-carbon quaternary stereocenters: synthetic and mechanistic studies of the C-acylation of silyl ketene acetals.

Authors: Ara H Mermerian; Gregory C Fu
Journal: J Am Chem Soc Date: 2005-04-20 Impact factor: 15.419

8. Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors: Kyle W Quasdorf; Larry E Overman
Journal: Nature Date: 2014-12-11 Impact factor: 49.962

9. Development of an air-stable nickel precatalyst for the amination of aryl chlorides, sulfamates, mesylates, and triflates.

Authors: Nathaniel H Park; Georgiy Teverovskiy; Stephen L Buchwald
Journal: Org Lett Date: 2013-11-27 Impact factor: 6.005

10. A stereoselective cyclization strategy for the preparation of γ-lactams and their use in the synthesis of α-methyl-β-proline.

Authors: Souvik Banerjee; Justin Smith; Jillian Smith; Caleb Faulkner; Douglas S Masterson
Journal: J Org Chem Date: 2012-11-12 Impact factor: 4.354

6 in total

6. Catalytic Enantioselective Synthesis of C₁ - and C₂ -Symmetric Spirobiindanones through Counterion-Directed Enolate C-Acylation.

Authors: Benjamin F Rahemtulla; Hugh F Clark; Martin D Smith
Journal: Angew Chem Int Ed Engl Date: 2016-10-10 Impact factor: 15.336