Literature DB >> 20578687

Enantioselective Wacker-type cyclization of 2-alkenyl-1,3-diketones promoted by Pd-SPRIX catalyst.

Kazuhiro Takenaka1, Suman C Mohanta, Mahesh L Patil, C V Laxman Rao, Shinobu Takizawa, Takeyuki Suzuki, Hiroaki Sasai.   

Abstract

An enantioselective intramolecular Wacker-type cyclization of 2-alkenyl-1,3-diketones catalyzed by a Pd(II)-SPRIX complex was developed. The reaction proceeded in a 6-endo-trig mode to give the desired chromene derivatives with moderate to good enantioselectivity. Isomerization of C-C double bonds via a pi-allyl Pd intermediate was involved as the key step.

Entities:  

Year:  2010        PMID： 20578687     DOI： 10.1021/ol1013069

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


  4 in total

Review 1.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

2.  Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

Authors:  Nicholas J Race; Cristiane S Schwalm; Takayuki Nakamuro; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-12-01       Impact factor: 15.419

3.  Syntheses of Amorfrutins and Derivatives via Tandem Diels-Alder and Anionic Cascade Approaches.

Authors:  Brian J Curtis; Robert J Micikas; Russell N Burkhardt; Rubin A Smith; Judy Y Pan; Katrina Jander; Frank C Schroeder
Journal:  J Org Chem       Date:  2021-03-04       Impact factor: 4.198

4.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-06-23       Impact factor: 15.419
  4 in total

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