Literature DB >> 12735759

High enantioselectivity in rhodium-catalyzed allylic alkylation of 1-substituted 2-propenyl acetates.

Tamio Hayashi1, Atsushi Okada, Toshimasa Suzuka, Motoi Kawatsura.   

Abstract

[reaction: see text] Rhodium-catalyzed asymmetric allylic alkylation of 1-substituted 2-propenyl acetates with dimethyl malonate proceeded with high enantioselectivity in the presence of cesium carbonate as a base and a rhodium catalyst generated from Rh(dpm)(C(2)H(4))(2) (dpm = dipivaloylmethanato) and a chiral phosphino-oxazoline whose basic skeleton is axially chiral binaphthyl to give branch alkylation products in greater than 90% ee.

Entities:  

Year:  2003        PMID: 12735759     DOI: 10.1021/ol0343562

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


  7 in total

1.  Mechanistic studies of the molybdenum-catalyzed asymmetric alkylation reaction.

Authors:  David L Hughes; Guy C Lloyd-Jones; Shane W Krska; Laure Gouriou; Veronique D Bonnet; Kevin Jack; Yongkui Sun; David J Mathre; Robert A Reamer
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-31       Impact factor: 11.205

2.  Recent Developments in Rhodium-Catalyzed Allylic Substitution and Carbocyclization Reactions.

Authors:  P Andrew Evans; David K Leahy
Journal:  Chemtracts       Date:  2003-08-01

Review 3.  Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors:  Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

4.  Iridium-catalyzed kinetic asymmetric transformations of racemic allylic benzoates.

Authors:  Levi M Stanley; Chen Bai; Mitsuhiro Ueda; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

5.  Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

Authors:  Faben A Cruz; Zhiwei Chen; Sarah I Kurtoic; Vy M Dong
Journal:  Chem Commun (Camb)       Date:  2016-04-04       Impact factor: 6.222

6.  Rhodium-catalysed asymmetric allylic arylation of racemic halides with arylboronic acids.

Authors:  Mireia Sidera; Stephen P Fletcher
Journal:  Nat Chem       Date:  2015-10-12       Impact factor: 24.427

Review 7.  Catalytic Asymmetric Hydroalkoxylation of C-C Multiple Bonds.

Authors:  Jennifer L Kennemur; Rajat Maji; Manuel J Scharf; Benjamin List
Journal:  Chem Rev       Date:  2021-12-03       Impact factor: 60.622

  7 in total

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