Literature DB >> 16986974

Nickel(0)-catalyzed asymmetric hydrocyanation of 1,3-dienes.

Biswajit Saha1, T V Rajanbabu.   

Abstract

1,2-Bis-diarylphosphinites are excellent ligands for the Ni(0)-catalyzed hydrocyanation of certain types of 1,3-dienes. 1-Phenyl-1,3-butadiene, 1-vinyl-3,4-dihydronaphthalene, and 1-vinylindene undergo highly regioselective hydrocyanation under ambient conditions to give exclusively the 1,2-adducts in good to excellent yields. Using bis-1,2-diarylphosphinites derived from d-glucose, the highest enantioselectivities to-date for asymmetric hydrocyanation of 1,3-dienes (70-83% ee's) have been obtained.

Entities:  

Year:  2006        PMID: 16986974     DOI: 10.1021/ol062002f

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


  8 in total

1.  Cationic Co(I)-Intermediates for Hydrofunctionalization Reactions: Regio- and Enantioselective Cobalt-Catalyzed 1,2-Hydroboration of 1,3-Dienes.

Authors:  Krishnaja Duvvuri; Kendra R Dewese; Mahesh M Parsutkar; Stanley M Jing; Milauni M Mehta; Judith C Gallucci; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-04-25       Impact factor: 15.419

Review 2.  Catalyzing Electrosynthesis: A Homogeneous Electrocatalytic Approach to Reaction Discovery.

Authors:  Juno C Siu; Niankai Fu; Song Lin
Journal:  Acc Chem Res       Date:  2020-02-20       Impact factor: 22.384

3.  Catalytic asymmetric synthesis of secondary nitriles via stereoconvergent Negishi arylations and alkenylations of racemic α-bromonitriles.

Authors:  Junwon Choi; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2012-05-21       Impact factor: 15.419

4.  Synthesis, crystal structure and investigation of mononuclear copper(II) and zinc(II) complexes of a new carboxylate rich tripodal ligand and their interaction with carbohydrates in alkaline aqueous solution.

Authors:  Christopher D Stewart; Mayra Pedraza; Hadi Arman; Hua-Jun Fan; Eduardo Luiz Schilling; Bruno Szpoganicz; Ghezai T Musie
Journal:  J Inorg Biochem       Date:  2015-04-30       Impact factor: 4.155

5.  Enantioselective Olefin Hydrocyanation without Cyanide.

Authors:  Alexander W Schuppe; Gustavo M Borrajo-Calleja; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-11-18       Impact factor: 15.419

6.  Asymmetric hydrovinylation of unactivated linear 1,3-dienes.

Authors:  Rakesh K Sharma; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

7.  In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors:  T V Rajanbabu
Journal:  Synlett       Date:  2009       Impact factor: 2.454

8.  Efficient, selective, and green: catalyst tuning for highly enantioselective reactions of ethylene.

Authors:  Craig R Smith; T V RajanBabu
Journal:  Org Lett       Date:  2008-03-20       Impact factor: 6.005

  8 in total

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