Literature DB >> 16173730

Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids.

Jean-François Fournier1, Simon Mathieu, André B Charette.   

Abstract

The highly diastereoselective zinco-cyclopropanation of chiral allylic alcohols using gem-dizinc carbenoids is described. The reaction produces three contiguous stereogenic centers, and the resulting chiral cyclopropylzinc derivatives can be trapped with electrophiles with retention of configuration. Simple functional group manipulations lead to the efficient synthesis of orthogonally protected 1,2,3-substituted cyclopropane derivatives.

Entities:  

Mesh:

Substances:

Year:  2005        PMID: 16173730     DOI: 10.1021/ja054328+

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  4 in total

1.  Diasteroselective preparation of cyclopropanols using methylene bis(iodozinc).

Authors:  Kevin Cheng; Patrick J Carroll; Patrick J Walsh
Journal:  Org Lett       Date:  2011-04-04       Impact factor: 6.005

2.  An asymmetric total synthesis of brevisamide.

Authors:  Arun K Ghosh; Jianfeng Li
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

3.  Formal and total synthesis of (±)-cycloclavine.

Authors:  Nitinkumar D Jabre; Teruki Watanabe; Matthias Brewer
Journal:  Tetrahedron Lett       Date:  2014-01-01       Impact factor: 2.415

4.  Highly enantio- and diastereoselective one-pot methods for the synthesis of halocyclopropyl alcohols.

Authors:  Hun Young Kim; Luca Salvi; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.