Literature DB >> 16354079

Palladium-catalyzed asymmetric amination and imidation of 2,3-allenyl phosphates.

Yasushi Imada1, Masayuki Nishida, Koji Kutsuwa, Shun-Ichi Murahashi, Takeshi Naota.   

Abstract

[reaction: see text] Asymmetric amination of 2,3-allenyl phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and imides can be performed efficiently using a combination of zerovalent palladium complexes and SEGPHOS or MeOBIPHEP ligand, affording the corresponding optically active 1-aminated derivatives with enantiomeric excess of up to 97% ee.

Entities:  

Year:  2005        PMID： 16354079     DOI： 10.1021/ol0523502

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


  6 in total

1.  Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors:  Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2012-12-04       Impact factor: 4.354

2.  Site- and enantioselective formation of allene-bearing tertiary or quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution.

Authors:  Byunghyuck Jung; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-03       Impact factor: 15.419

3.  Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors:  Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2019-05-15       Impact factor: 15.419

4.  Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes.

Authors:  Qian Yao; Yuting Liao; Lili Lin; Xiaobin Lin; Jie Ji; Xiaohua Liu; Xiaoming Feng
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

5.  Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.

Authors:  Liela Bayeh-Romero; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-08-21       Impact factor: 15.419

6.  Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes.

Authors:  Shihua Song; Jing Zhou; Chunling Fu; Shengming Ma
Journal:  Nat Commun       Date:  2019-01-31       Impact factor: 14.919
  6 in total

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