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Literature DB >> 10823188

Catalytic enantioselective amination of enolsilanes using C2-symmetric copper(II) complexes as chiral Lewis acids.

Abstract

[formula: see text] [Cu(S,S)-t-Bu-box](OTf)2 (1) catalyzes the enantioselective amination of enolsilanes with azodicarboxylate derivatives. Isomerically pure enolsilanes of aryl ketones, acylpyrroles, and thioesters added to the azo-imide in greater than 95% ee. The use of an alcohol additive was critical to achieving catalyst turnover.

Entities: Chemical Gene

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Year: 1999 PMID： 10823188 DOI： 10.1021/ol990113r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

12 in total

1. α-Amination of keto-nitrones via multihetero-Cope rearrangement employing an imidoyl chloride reagent.

Authors: Justin T Malinowski; Ericka J Malow; Jeffrey S Johnson
Journal: Chem Commun (Camb) Date: 2012-06-26 Impact factor: 6.222

2. Total synthesis of laulimalide: synthesis of the northern and southern fragments.

Authors: Barry M Trost; W Michael Seganish; Cheol K Chung; Dominique Amans
Journal: Chemistry Date: 2012-02-03 Impact factor: 5.236

3. Type 2 intramolecular N-acylazo Diels-Alder reaction: regio- and stereoselective synthesis of bridgehead bicyclic 1,2-diazines.

Authors: Claudia L Molina; Chun P Chow; Kenneth J Shea
Journal: J Org Chem Date: 2007-08-04 Impact factor: 4.354

4. Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

Authors: Hideyuki Konishi; Tin Yiu Lam; Jeremiah P Malerich; Viresh H Rawal
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

Catalytic enantioselective amination of enolsilanes using C2-symmetric copper(II) complexes as chiral Lewis acids.

1. α-Amination of keto-nitrones via multihetero-Cope rearrangement employing an imidoyl chloride reagent.

2. Total synthesis of laulimalide: synthesis of the northern and southern fragments.

3. Type 2 intramolecular N-acylazo Diels-Alder reaction: regio- and stereoselective synthesis of bridgehead bicyclic 1,2-diazines.

4. Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

5. Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade.

6. Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.

7. Nitrene-mediated intermolecular N-N coupling for efficient synthesis of hydrazides.

8. Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes.

Review 9. Control of asymmetry in the radical addition approach to chiral amine synthesis.

10. Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.