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Literature DB >> 21180720

Ammonium ylides for the diastereoselective synthesis of glycidic amides.

Mario Waser¹, Richard Herchl, Norbert Müller.

Abstract

A highly trans-selective protocol for the synthesis of glycidic amides was developed. This approach gave access to oxiranes by reacting stabilised ammonium ylides bearing an α-carbonyl group and aromatic aldehydes in moderate to good yields.

Entities: Chemical

Year: 2010 PMID： 21180720 PMCID： PMC4202193 DOI： 10.1039/c0cc04821f

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

18 in total

1. A catalytic cycle for the asymmetric synthesis of epoxides using sulfur ylides.

Authors: J Zanardi; C Leriverend; D Aubert; K Julienne; P Metzner
Journal: J Org Chem Date: 2001-08-10 Impact factor: 4.354

2. Organic-catalyst-mediated cyclopropanation reaction.

Authors: Charles D Papageorgiou; Steven V Ley; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2003-02-17 Impact factor: 15.336

3. Enantioselective organocatalytic cyclopropanation via ammonium ylides.

Authors: Charles D Papageorgiou; Maria A Cubillo de Dios; Steven V Ley; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2004-09-06 Impact factor: 15.336

4. Enantioselective catalytic intramolecular cyclopropanation using modified cinchona alkaloid organocatalysts.

Authors: Carin C C Johansson; Nadine Bremeyer; Steven V Ley; Dafydd R Owen; Stephen C Smith; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2006-09-11 Impact factor: 15.336

Review 5. Recent developments in the use of catalytic asymmetric ammonium enolates in chemical synthesis.

Authors: Matthew J Gaunt; Carin C C Johansson
Journal: Chem Rev Date: 2007-12 Impact factor: 60.622

6. An intramolecular organocatalytic cyclopropanation reaction.

Authors: Nadine Bremeyer; Stephen C Smith; Steven V Ley; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2004-05-10 Impact factor: 15.336

7. On the importance of leaving group ability in reactions of ammonium, oxonium, phosphonium, and sulfonium ylides.

Authors: Varinder K Aggarwal; Jeremy N Harvey; Raphaël Robiette
Journal: Angew Chem Int Ed Engl Date: 2005-08-26 Impact factor: 15.336

8. Highly enantioselective synthesis of isoxazoline N-oxides.

Authors: Chun-Yin Zhu; Xian-Ming Deng; Xiu-Li Sun; Jun-Cheng Zheng; Yong Tang
Journal: Chem Commun (Camb) Date: 2008-02-14 Impact factor: 6.222

9. Strained azetidinium ylides: new reagents for epoxidation.

Authors: Audrey Alex; Bénédicte Larmanjat; Jérôme Marrot; François Couty; Olivier David
Journal: Chem Commun (Camb) Date: 2007-03-22 Impact factor: 6.222

10. Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis.

Authors: Varinder K Aggarwal; Jonathan P H Charmant; Daniel Fuentes; Jeremy N Harvey; George Hynd; Diasuke Ohara; Willy Picoul; Raphaël Robiette; Catherine Smith; Jean-Luc Vasse; Caroline L Winn
Journal: J Am Chem Soc Date: 2006-02-15 Impact factor: 15.419

11 in total

1. Identification of the best-suited leaving group for the diastereoselective synthesis of glycidic amides from stabilised ammonium ylides and aldehydes.

Authors: Richard Herchl; Martin Stiftinger; Mario Waser
Journal: Org Biomol Chem Date: 2011-08-11 Impact factor: 3.876

2. Benzylic Ammonium Ylide Mediated Epoxidations.

Authors: Lukas Roiser; Raphaël Robiette; Mario Waser
Journal: Synlett Date: 2016-06-15 Impact factor: 2.454

3. Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides.

Authors: Mathias Pichler; Johanna Novacek; Raphaël Robiette; Vanessa Poscher; Markus Himmelsbach; Uwe Monkowius; Norbert Müller; Mario Waser
Journal: Org Biomol Chem Date: 2015-02-21 Impact factor: 3.876

4. Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions.

Authors: Johanna Novacek; Lukas Roiser; Katharina Zielke; Raphaël Robiette; Mario Waser
Journal: Chemistry Date: 2016-07-06 Impact factor: 5.236

5. On the origin of the stereoselectivity in chiral amide-based ammonium ylide-mediated epoxidations.

Authors: Johanna Novacek; Raphaël Robiette; Mario Waser
Journal: Monatsh Chem Date: 2016-11-24 Impact factor: 1.451

6. Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o-Quinone Methides.

Authors: Nicole Meisinger; Lukas Roiser; Uwe Monkowius; Markus Himmelsbach; Raphaël Robiette; Mario Waser
Journal: Chemistry Date: 2017-03-27 Impact factor: 5.236