Literature DB >> 10825978

Mechanism and conditions for highly enantioselective epoxidation of alpha,beta-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt.

E J Corey1, F Y Zhang.   

Abstract

[formula: see text] Highly enantioselective (up to 130:1) epoxidation of a variety of alpha,beta-enones to form alpha,beta-epoxy ketones is described along with a rational analysis of the mechanistic basis for this strong absolute stereochemical control by the chiral catalyst 2.

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Year:  1999        PMID： 10825978     DOI： 10.1021/ol990964z

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


  10 in total

1.  Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis-Naphthoquinones.

Authors:  Chao Qi; Wenyu Wang; Kyle D Reichl; James McNeely; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-29       Impact factor: 15.336

2.  Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones.

Authors:  Xiaojie Lu; Yan Liu; Bingfeng Sun; Brittany Cindric; Li Deng
Journal:  J Am Chem Soc       Date:  2008-06-05       Impact factor: 15.419

Review 3.  Chalcone: A Privileged Structure in Medicinal Chemistry.

Authors:  Chunlin Zhuang; Wen Zhang; Chunquan Sheng; Wannian Zhang; Chengguo Xing; Zhenyuan Miao
Journal:  Chem Rev       Date:  2017-05-10       Impact factor: 60.622

4.  Iron(II)-Catalyzed Asymmetric Epoxidation of Trisubstituted α,β-Unsaturated Esters.

Authors:  Lan Luo; Hisashi Yamamoto
Journal:  European J Org Chem       Date:  2014-12

5.  Enantioselective linchpin catalysis by SOMO catalysis: an approach to the asymmetric alpha-chlorination of aldehydes and terminal epoxide formation.

Authors:  Muriel Amatore; Teresa D Beeson; Sean P Brown; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Enantioselective iodolactonization of disubstituted olefinic acids using a bifunctional catalyst.

Authors:  Chao Fang; Daniel H Paull; J Caleb Hethcox; Christopher R Shugrue; Stephen F Martin
Journal:  Org Lett       Date:  2012-11-30       Impact factor: 6.005

7.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

8.  Cascade annulation reaction (CAR): highly diastereoselective synthesis of pyranopyrazole scaffolds.

Authors:  Manickam Bakthadoss; Manickam Surendar
Journal:  RSC Adv       Date:  2020-05-19       Impact factor: 4.036

9.  Sterically Demanding Flexible Phosphoric Acids for Constructing Efficient and Multi-Purpose Asymmetric Organocatalysts.

Authors:  Fabian Scharinger; Ádám Márk Pálvölgyi; Melanie Weisz; Matthias Weil; Christian Stanetty; Michael Schnürch; Katharina Bica-Schröder
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-26       Impact factor: 16.823

10.  Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts.

Authors:  Maciej Majdecki; Agata Tyszka-Gumkowska; Janusz Jurczak
Journal:  Org Lett       Date:  2020-10-28       Impact factor: 6.005
  10 in total

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