Literature DB >> 24155160

One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: highly selective formation of three new bonds and two stereocenters in acyclic systems.

Polina Smirnov1, Jomon Mathew, Anne Nijs, Einat Katan, Miriam Karni, Carsten Bolm, Yitzhak Apeloig, Ilan Marek.   

Abstract

It's as easy as 1, 2, 3: In a one-pot sequence, two stereocenters and three new bonds were created with high selectivity through an asymmetric alkynylation of acyl silanes, a tandem Brook-type rearrangement and Zn-ene-allene cyclization, the addition of an electrophile, and finally oxidation. The straightforward nature of the synthetic procedure contrasts strongly with the complexity of the densely functionalized products obtained.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brook rearrangement; acyl silanes; alkynylation; asymmetric synthesis; zinc

Year:  2013        PMID: 24155160     DOI: 10.1002/anie.201306749

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


  2 in total

1.  Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry.

Authors:  Kevin T O'Brien; Amos B Smith
Journal:  Org Lett       Date:  2019-09-09       Impact factor: 6.005

2.  ProPhenol-catalyzed asymmetric additions by spontaneously assembled dinuclear main group metal complexes.

Authors:  Barry M Trost; Mark J Bartlett
Journal:  Acc Chem Res       Date:  2015-02-04       Impact factor: 22.384

  2 in total

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