Literature DB >> 25867945

Catalytic enantioselective intramolecular aza-diels-alder reactions.

Chang Min1, Chih-Tsung Lin1, Daniel Seidel2.   

Abstract

A readily available chiral Brønsted acid was identified as an efficient catalyst for intramolecular Povarov reactions. Polycyclic amines containing three contiguous stereogenic centers were obtained with excellent stereocontrol in a single step from secondary anilines and aldehydes possessing a pendent dienophile. These transformations constitute the first examples of catalytic enantioselective intramolecular aza-Diels-Alder reactions.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brønsted acids; asymmetric catalysis; cycloaddition; ion pairs; organocatalysis

Year:  2015        PMID： 25867945     DOI： 10.1002/anie.201501536

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  2 in total

1.  Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors:  Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

2.  Strong Brønsted acid promoted asymmetric hydrogenation of isoquinolines and quinolines catalyzed by a Rh-thiourea chiral phosphine complex via anion binding.

Authors:  Jialin Wen; Renchang Tan; Shaodong Liu; Qingyang Zhao; Xumu Zhang
Journal:  Chem Sci       Date:  2016-01-26       Impact factor: 9.825
  2 in total

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