Literature DB >> 29710968

Catalytic Asymmetric Allenylation: Regulation of the Equilibrium between Propargyl- and Allenylstannanes during the Catalytic Process.

Chan-Mo Yu1, Sook-Kyung Yoon1, Kwangwoo Baek1, Jae-Young Lee1.   

Abstract

Achiral substrates 1 and 2 can be regioselectively converted into chiral allenyl alcohols 3 through the title reaction [Eq. (1)] with the synergetic reagent iPrSBEt2 and a chiral TiIV catalyst. The dramatic regioselectivity originates from the regulation of the equilibrium between propargyl- and allenylstannanes during the catalytic process. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Aldehydes; Asymmetric catalysis; Lewis acids; Synthetic methods; Titanium

Year:  1998        PMID: 29710968     DOI: 10.1002/(SICI)1521-3773(19980918)37:17<2392::AID-ANIE2392>3.0.CO;2-D

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


  4 in total

1.  C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

Authors:  Tao Liang; Sang Kook Woo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

2.  A Computational Investigation of the Ligand-Controlled Cu-Catalyzed Site-Selective Propargylation and Allenylation of Carbonyl Compounds.

Authors:  Yike Zou; Osvaldo Gutierrez; Avery C Sader; Nitinchandra D Patel; Daniel R Fandrick; Carl A Busacca; Keith R Fandrick; Marisa Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2017-11-02       Impact factor: 6.005

3.  Enzyme- and Ruthenium-Catalyzed Enantioselective Transformation of α-Allenic Alcohols into 2,3-Dihydrofurans.

Authors:  Bin Yang; Can Zhu; Youai Qiu; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-08       Impact factor: 15.336

4.  Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation.

Authors:  Jucleiton J R Freitas; Queila P S B Freitas; Silvia R C P Andrade; Juliano C R Freitas; Roberta A Oliveira; Paulo H Menezes
Journal:  Beilstein J Org Chem       Date:  2020-02-04       Impact factor: 2.883

  4 in total

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