Literature DB >> 21361355

Organocatalytic approach to polysubstituted piperidines and tetrahydropyrans.

You Wang1, Shaolin Zhu, Dawei Ma.   

Abstract

Polysubstituted piperidines and tetrahydropyrans are synthesized from aldehydes and two classes of trisubstituted nitroolefins via an O-TMS protected diphenylprolinol catalyzed domino Michael addition/aminalization (or acetalization) process. This approach allows formation of four contiguous stereocenters in the piperidine or tetrahydropyran ring in one step with excellent enantioselectivity.

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Year:  2011        PMID： 21361355     DOI： 10.1021/ol200004s

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


  4 in total

1.  A catalytic asymmetric synthesis of polysubstituted piperidines using a rhodium(I)-catalyzed [2+2+2] cycloaddition employing a cleavable tether.

Authors:  Timothy J Martin; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-19       Impact factor: 15.336

2.  Asymmetric Synthesis of Functionalized Dihydro- and Tetrahydropyrans via an Organocatalytic Domino Michael-Hemiacetalization Reaction.

Authors:  Gregor Urbanietz; Iuliana Atodiresei; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-05-01       Impact factor: 3.157

3.  A new approach toward the total synthesis of (+)-batzellaside B.

Authors:  Jolanta Wierzejska; Shin-Ichi Motogoe; Yuto Makino; Tetsuya Sengoku; Masaki Takahashi; Hidemi Yoda
Journal:  Beilstein J Org Chem       Date:  2012-10-25       Impact factor: 2.883

4.  Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Beilstein J Org Chem       Date:  2013-06-12       Impact factor: 2.883
  4 in total

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