Literature DB >> 18850717

Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts.

Ethan Alden-Danforth1, Michael T Scerba, Thomas Lectka.   

Abstract

The catalytic, enantioselective, [4 + 2] cycloaddition reaction of ortho-quinone methides with silyl ketene acetals is described. This mechanistically interesting reaction, initiated by a chiral cinchona alkaloid-derived ammonium fluoride "precatalyst" complex, affords a variety of alkyl- and aryl-substituted 3,4-dihydrocoumarin products in excellent yield and with good enantioselectivity.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18850717      PMCID： PMC2652256          DOI： 10.1021/ol802029e

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


  10 in total

1.  Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.

Authors:  L M Tillekeratne; A Sherette; P Grossman; L Hupe; D Hupe; R A Hudson
Journal:  Bioorg Med Chem Lett       Date:  2001-10-22       Impact factor: 2.823

2.  Catalytic, asymmetric synthesis of 1,4-benzoxazinones: a remarkably enantioselective route to alpha-amino acid derivatives from o-benzoquinone imides.

Authors:  Jamison Wolfer; Tefsit Bekele; Ciby J Abraham; Cajetan Dogo-Isonagie; Thomas Lectka
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-13       Impact factor: 15.336

Review 3.  Recent advances in asymmetric phase-transfer catalysis.

Authors:  Takashi Ooi; Keiji Maruoka
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 4.  Recent development and application of chiral phase-transfer catalysts.

Authors:  Takuya Hashimoto; Keiji Maruoka
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

5.  Photoactivation of amino-substituted 1,4-benzoquinones for release of carboxylate and phenolate leaving groups using visible light.

Authors:  Yugang Chen; Mark G Steinmetz
Journal:  J Org Chem       Date:  2006-08-04       Impact factor: 4.354

6.  Catalytic, enantioselective bifunctional inverse electron demand hetero-Diels-Alder reactions of ketene enolates and o-benzoquinone diimides.

Authors:  Ciby J Abraham; Daniel H Paull; Michael T Scerba; James W Grebinski; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

7.  Structure-activity correlation of flavonoids for inhibition of bovine lens aldose reductase.

Authors:  M Iinuma; T Tanaka; M Mizuno; T Katsuzaki; H Ogawa
Journal:  Chem Pharm Bull (Tokyo)       Date:  1989-07       Impact factor: 1.645

8.  Suicide inactivation of human prostatic acid phosphatase and a phosphotyrosine phosphatase.

Authors:  Q Wang; U Dechert; F Jirik; S G Withers
Journal:  Biochem Biophys Res Commun       Date:  1994-04-15       Impact factor: 3.575

9.  Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: efficient entry to chiral, alpha-oxygenated carboxylic acid derivatives.

Authors:  Tefsit Bekele; Meha H Shah; Jamison Wolfer; Ciby J Abraham; Anthony Weatherwax; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2006-02-15       Impact factor: 15.419

10.  Photoaddition of water and alcohols to the anthracene moiety of 9-(2'-hydroxyphenyl)anthracene via formal excited state intramolecular proton transfer.

Authors:  Mitchel Flegel; Matthew Lukeman; Lawrence Huck; Peter Wan
Journal:  J Am Chem Soc       Date:  2004-06-30       Impact factor: 15.419
  10 in total
  16 in total

1.  A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Authors:  Kun Liu; M Todd Hovey; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-10-01       Impact factor: 9.825

2.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

3.  Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.

Authors:  Robert S Lewis; Christopher J Garza; Ann T Dang; Te Kie A Pedro; William J Chain
Journal:  Org Lett       Date:  2015-04-23       Impact factor: 6.005

4.  Diastereoselective Synthesis of trans-beta-Lactams Using a Simple Multifunctional Catalyst.

Authors:  Ciby J Abraham; Daniel H Paull; Cajetan Dogo-Isonagie; Thomas Lectka
Journal:  Synlett       Date:  2009       Impact factor: 2.454

5.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

6.  Development of an alkaloid-pyrone annulation: synthesis of pleiomaltinine.

Authors:  Robert E Ziegler; Shin-Jowl Tan; Toh-Seok Kam; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-15       Impact factor: 15.336

7.  Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts.

Authors:  Satish Jakkampudi; Ramarao Parella; John C-G Zhao
Journal:  Org Biomol Chem       Date:  2018-12-19       Impact factor: 3.876

8.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005

9.  Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Authors:  Yi Luan; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

10.  Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.

Authors:  Chirag D Gheewala; Jennifer S Hirschi; Wai-Hang Lee; Daniel W Paley; Mathew J Vetticatt; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2018-03-06       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.