Literature DB >> 25689601

Cyclopropene derivatives as precursors to enantioenriched cyclopropanols and n-butenals possessing quaternary carbon stereocenters.

Marwan Simaan1, Pierre-Olivier Delaye1, Min Shi2, Ilan Marek3.   

Abstract

The diastereoselective carbocupration reaction of cyclopropenylmethyl ethers followed by addition of oxenoid leads to the formation of diastereo- and enantiomerically enriched 2,2,3,3-tetrasubstituted cyclopropanol derivatives. Ring fragmentation of the copper cyclopropanolate leads to acyclic butenal derivatives possessing enantiomerically enriched α-quaternary carbon stereocenters in a single-pot operation.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; metalation; small-ring systems; strained molecules; synthetic methods

Year:  2015        PMID: 25689601     DOI: 10.1002/anie.201412440

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


  12 in total

1.  Cyclopropenes in Metallacycle-Mediated Cross-Coupling with Alkynes: Convergent Synthesis of Highly Substituted Vinylcyclopropanes.

Authors:  Natasha F O'Rourke; Glenn C Micalizio
Journal:  Org Lett       Date:  2016-03-01       Impact factor: 6.005

2.  Directed nucleophilic addition of phenoxides to cyclopropenes.

Authors:  Pavel Yamanushkin; Michael Lu-Diaz; Andrew Edwards; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2017-10-04       Impact factor: 3.876

3.  Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

Authors:  Vladimir Maslivetc; Colby Barrett; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2018-01-03       Impact factor: 3.876

4.  Zirconocene catalyzed diastereoselective carbometalation of cyclobutenes.

Authors:  Sudipta Raha Roy; Hendrik Eijsberg; Jeffrey Bruffaerts; Ilan Marek
Journal:  Chem Sci       Date:  2016-08-30       Impact factor: 9.825

5.  Efficient and stereodivergent synthesis of unsaturated acyclic fragments bearing contiguous stereogenic elements.

Authors:  Jeffrey Bruffaerts; David Pierrot; Ilan Marek
Journal:  Nat Chem       Date:  2018-08-27       Impact factor: 24.427

6.  Diastereo- and enantioselective copper catalyzed hydroallylation of disubstituted cyclopropenes.

Authors:  Heiko Sommer; Ilan Marek
Journal:  Chem Sci       Date:  2018-07-02       Impact factor: 9.825

7.  Diastereo- and enantioselective preparation of cyclopropanol derivatives.

Authors:  Marwan Simaan; Ilan Marek
Journal:  Beilstein J Org Chem       Date:  2019-03-21       Impact factor: 2.883

8.  Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation.

Authors:  Veeranjaneyulu Lanke; Fa-Guang Zhang; Alexander Kaushansky; Ilan Marek
Journal:  Chem Sci       Date:  2019-08-27       Impact factor: 9.825

Review 9.  Copper mediated carbometalation reactions.

Authors:  D S Müller; I Marek
Journal:  Chem Soc Rev       Date:  2016-08-08       Impact factor: 54.564

10.  Diastereodivergent combined carbometalation/zinc homologation/C-C fragmentation reaction as an efficient tool to prepare acyclic allylic quaternary carbon stereocenters.

Authors:  Sudipta Raha Roy; Dorian Didier; Amir Kleiner; Ilan Marek
Journal:  Chem Sci       Date:  2016-05-24       Impact factor: 9.825

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