Literature DB >> 20936058

Lewis Acid-Promoted Mukaiyama Aldol-Prins (MAP) Cyclizations of Acetals, Ketals, α-Acetoxy Ethers, and Orthoformates.

Michael R Gesinski1, Lori J Van Orden, Scott D Rychnovsky.   

Abstract

The Mukaiyama aldol-Prins (MAP) cyclization of acetals stereoselectively provided substituted tetrahydropyrans. The scope of the reaction has been expanded to include other electrophiles, including ketals and α-acetoxy ethers. Finally, a double MAP cyclization with orthoformates is described.

Entities:  

Year:  2008        PMID： 20936058      PMCID： PMC2951841          DOI： 10.1055/s-2008-1032053

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


  10 in total

1.  Mukaiyama aldol-Prins cyclization cascade reaction: a formal total synthesis of leucascandrolide A.

Authors:  D J Kopecky; S D Rychnovsky
Journal:  J Am Chem Soc       Date:  2001-08-29       Impact factor: 15.419

2.  Strategic use of pinacol-terminated Prins cyclizations in target-oriented total synthesis.

Authors:  Larry E Overman; Lewis D Pennington
Journal:  J Org Chem       Date:  2003-09-19       Impact factor: 4.354

3.  Synthesis of highly substituted cyclohexenes via mixed Lewis acid-catalyzed Diels-Alder reactions of highly substituted dienes and dienophiles.

Authors:  Michael E Jung; David Ho; Hiufung V Chu
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

4.  Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking Prins with Cope and Grob.

Authors:  Roger W Alder; Jeremy N Harvey; Mark T Oakley
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

5.  Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.

Authors:  Leticia Ayala; Claudia G Lucero; Jan Antoinette C Romero; Sarah A Tabacco; K A Woerpel
Journal:  J Am Chem Soc       Date:  2003-12-17       Impact factor: 15.419

6.  Titanium(IV)-promoted Mukaiyama aldol-Prins cyclizations.

Authors:  Brian Patterson; Shinji Marumoto; Scott D Rychnovsky
Journal:  Org Lett       Date:  2003-08-21       Impact factor: 6.005

7.  Total synthesis of leucascandrolide a: a new application of the Mukaiyama aldol-Prins reaction.

Authors:  Lori J Van Orden; Brian D Patterson; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2007-06-27       Impact factor: 4.354

8.  Diastereoselective additions of nucleophiles to alpha-acetoxy ethers using the alpha-(trimethylsilyl)benzyl auxiliary.

Authors:  Scott D Rychnovsky; Jennifer Cossrow
Journal:  Org Lett       Date:  2003-06-26       Impact factor: 6.005

9.  Axial-selective prins cyclizations by solvolysis of alpha-bromo ethers.

Authors:  Ramesh Jasti; Justin Vitale; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

10.  Syn- and anti-selective Prins cyclizations of delta,epsilon-unsaturated ketones to 1,3-halohydrins with Lewis acids.

Authors:  R Brandon Miles; Chad E Davis; Robert M Coates
Journal:  J Org Chem       Date:  2006-02-17       Impact factor: 4.354
  10 in total
  4 in total

1.  Assignment of absolute configuration to SCH 351448 via total synthesis.

Authors:  Lael L Cheung; Shinji Marumoto; Christopher D Anderson; Scott D Rychnovsky
Journal:  Org Lett       Date:  2008-06-11       Impact factor: 6.005

2.  Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.

Authors:  Robert J Hinkle; Shane E Lewis
Journal:  Org Lett       Date:  2013-08-01       Impact factor: 6.005

3.  Cu(II)-catalyzed olefin migration and Prins cyclization: highly diastereoselective synthesis of substituted tetrahydropyrans.

Authors:  Arun K Ghosh; Daniel R Nicponski
Journal:  Org Lett       Date:  2011-07-28       Impact factor: 6.005

4.  Diastereoselective Synthesis of Substituted Tetrahydropyrans by Copper(II)-Bisphosphine-Catalyzed Olefin Migration and Prins Cyclization.

Authors:  Arun K Ghosh; Jorden Kass; Daniel R Nicponski; Chad Keyes
Journal:  Synthesis (Stuttg)       Date:  2012-12       Impact factor: 3.157
  4 in total

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