Literature DB >> 25960607

Stereoselective Synthesis of Dioxolanes and Oxazolidines via a Desymmetrization Acetalization/Michael Cascade.

David M Rubush1, Tomislav Rovis1.   

Abstract

The desymmetrization of p-quinols using a Brønsted acid catalyzed acetalization/Michael cascade was achieved in high yields and diastereoselectivities for aldehydes and imines. Use of a chiral Brønsted acid allowed for the synthesis of 1,3-dioxolane and 1,3-oxazolidine products in modest enantioselectivity.

Entities:  

Keywords:  Michael addition; acetals; cascade catalysis; desymmetrization; stereoselective synthesis

Year:  2014        PMID： 25960607      PMCID： PMC4422513          DOI： 10.1055/s-0033-1340669

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  20 in total

1.  Desymmetrization by ring-closing metathesis leading to 6,8-dioxabicyclo[3.2.1]octanes: a new route for the synthesis of (+)-exo- and endo-brevicomin.

Authors:  S D Burke; N Müller; C M Beaudry
Journal:  Org Lett       Date:  1999-12-02       Impact factor: 6.005

2.  Catalytic asymmetric transacetalization.

Authors:  Ilija Corić; Sreekumar Vellalath; Benjamin List
Journal:  J Am Chem Soc       Date:  2010-06-30       Impact factor: 15.419

3.  Kinetic resolution of homoaldols via catalytic asymmetric transacetalization.

Authors:  Ilija Čorić; Steffen Müller; Benjamin List
Journal:  J Am Chem Soc       Date:  2010-11-18       Impact factor: 15.419

4.  Concise enantioselective synthesis of the ten-membered lactone cephalosporolide G and its C-3 epimer.

Authors:  Silvia Barradas; Antonio Urbano; M Carmen Carreño
Journal:  Chemistry       Date:  2009-09-21       Impact factor: 5.236

5.  An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors:  David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

6.  Asymmetric spiroacetalization catalysed by confined Brønsted acids.

Authors:  Ilija Čorić; Benjamin List
Journal:  Nature       Date:  2012-03-14       Impact factor: 49.962

7.  Novel asymmetric oxy-michael addition reaction of the chiral ketones to the achiral gamma--or delta-hydroxy-alpha,beta-unsaturated carbonyl compounds.

Authors:  H Watanabe; K Machida; D Itoh; H Nagatsuka; T Kitahara
Journal:  Chirality       Date:  2001-07       Impact factor: 2.437

8.  Diastereoselective construction of syn-1,3-dioxanes via a bismuth-mediated two-component hemiacetal/oxa-conjugate addition reaction.

Authors:  P Andrew Evans; Aleksandr Grisin; Michael J Lawler
Journal:  J Am Chem Soc       Date:  2012-02-01       Impact factor: 15.419

9.  Oxidative de-aromatization of para-alkyl phenols into para-peroxyquinols and para-quinols mediated by oxone as a source of singlet oxygen.

Authors:  M Carmen Carreño; Marcos González-López; Antonio Urbano
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-21       Impact factor: 15.336

10.  Direct stereocontrolled synthesis of polyoxygenated hydrobenzofurans and hydrobenzopyrans from p-peroxy quinols.

Authors:  Silvia Barradas; M Carmen Carreño; Marcos Gonzalez-López; Alfonso Latorre; Antonio Urbano
Journal:  Org Lett       Date:  2007-11-01       Impact factor: 6.005
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  1 in total

1.  Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

Authors:  Banruo Huang; Ying He; Mark D Levin; Jaime A S Coelho; Robert G Bergman; F Dean Toste
Journal:  Adv Synth Catal       Date:  2019-09-06       Impact factor: 5.837
  1 in total

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