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Literature DB >> 22968901

Silyl ketene imines: highly versatile nucleophiles for catalytic, asymmetric synthesis.

Abstract

This Minireview provides an overview on the development of silyl ketene iminesn> and their recent applications in catalytic, enantioselective reactions. The unique structure of the ketene imine allows a diverse range of reactivity patterns and provides solutions to existing challenges in the enantioselective construction of quaternary stereogenic carbon centers and cross-benzoin adducts. A variety of reactions for which silyl ketene imines have been applied are presented with an overall goal of inspiring new uses for these underutilized nucleophiles.

Entities: Chemical Disease Gene

Year: 2012 PMID： 22968901 PMCID： PMC3532842 DOI： 10.1002/anie.201202139

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

50 in total

1. Extending mechanistic routes in heterazolium catalysis--promising concepts for versatile synthetic methods.

Authors: Kirsten Zeitler
Journal: Angew Chem Int Ed Engl Date: 2005-11-25 Impact factor: 15.336

2. Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors: John F Hartwig; Levi M Stanley
Journal: Acc Chem Res Date: 2010-09-28 Impact factor: 22.384

Review 3. Advances in acyl anion and homoenolate catalysis.

Authors: Jeffrey S Johson
Journal: Curr Opin Drug Discov Devel Date: 2007-11

Review 4. Organocatalysis by N-heterocyclic carbenes.

Authors: Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal: Chem Rev Date: 2007-10-23 Impact factor: 60.622

5. Catalytic asymmetric acylation of (silyloxy)nitrile anions.

Authors: David A Nicewicz; Christopher M Yates; Jeffrey S Johnson
Journal: Angew Chem Int Ed Engl Date: 2004-05-10 Impact factor: 15.336

6. Lewis base activation of Lewis acids: catalytic, enantioselective addition of silyl ketene acetals to aldehydes.

Authors: Scott E Denmark; Gregory L Beutner; Thomas Wynn; Martin D Eastgate
Journal: J Am Chem Soc Date: 2005-03-23 Impact factor: 15.419

7. Simple and efficient preparation of [10,20-13C2]- and [10-CH3,13-13C2]-10-methylretinal: introduction of substituents at the 2-position of 2,3-unsaturated nitriles.

Authors: P J Verdegem; M C Monnee; J Lugtenburg
Journal: J Org Chem Date: 2001-02-23 Impact factor: 4.354

8. 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

9. Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts.

Authors: Aurélien Bigot; Alice E Williamson; Matthew J Gaunt
Journal: J Am Chem Soc Date: 2011-08-17 Impact factor: 15.419

10. Enantioselective construction of quaternary stereogenic carbons by the Lewis base catalyzed additions of silyl ketene imines to aldehydes.

Authors: Scott E Denmark; Tyler W Wilson; Matthew T Burk; John R Heemstra
Journal: J Am Chem Soc Date: 2007-11-08 Impact factor: 15.419

5 in total

1. Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors: Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal: Angew Chem Int Ed Engl Date: 2013-10-15 Impact factor: 15.336

2. Catalytic Asymmetric Mannich Reaction of α-Fluoronitriles with Ketimines: Enantioselective and Diastereodivergent Construction of Vicinal Tetrasubstituted Stereocenters.

Authors: Ransheng Ding; Zeus A De Los Santos; Christian Wolf
Journal: ACS Catal Date: 2019-02-06 Impact factor: 13.084