Literature DB >> 14725443

A novel class of tunable zinc reagents (RXZnCH2Y) for efficient cyclopropanation of olefins.

Jon C Lorenz1, Jiang Long, Zhiqiang Yang, Song Xue, Yinong Xie, Yian Shi.   

Abstract

A class of zinc reagents (RXZnCH(2)Y) generated with an appropriate organozinc is very effective for the cyclopropanation of olefins. The reactivity and selectivity of these reagents can be regulated by tuning the electronic and steric nature of the RX group on Zn. A reasonable level of enantioselectivity was obtained for the cyclopropanation of unfunctionalized olefins when a chiral (iodomethyl)zinc species was used, providing a valuable approach for the asymmetric cyclopropanation of unfunctionalized olefins.

Entities:  

Year:  2004        PMID： 14725443     DOI： 10.1021/jo030312v

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  15 in total

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Authors:  Mohammad Hassam; Adriaan E Basson; Dennis C Liotta; Lynn Morris; Willem A L van Otterlo; Stephen C Pelly
Journal:  ACS Med Chem Lett       Date:  2012-05-02       Impact factor: 4.345

4.  O-Cyclopropyl hydroxylamines: gram-scale synthesis and utility as precursors for N-heterocycles.

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Journal:  Org Biomol Chem       Date:  2020-05-06       Impact factor: 3.876

5.  Stereoselective synthesis of β-hydroxy enamines, aminocyclopropanes, and 1,3-amino alcohols via asymmetric catalysis.

Authors:  Petr Valenta; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

6.  Carbonylative N-Heterocyclization via Nitrogen-Directed C-C Bond Activation of Nonactivated Cyclopropanes.

Authors:  Adam D J Calow; David Dailler; John F Bower
Journal:  J Am Chem Soc       Date:  2022-06-17       Impact factor: 16.383

7.  Applications of 1-alkenyl-1,1-heterobimetallics in the stereoselective synthesis of cyclopropylboronate esters, trisubstituted cyclopropanols and 2,3-disubstituted cyclobutanones.

Authors:  Mahmud M Hussain; Hongmei Li; Nusrah Hussain; Mercedes Ureña; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2009-05-13       Impact factor: 15.419

8.  Cu(I)-catalyzed diamination of conjugated olefins with tunable anionic counterions. A possible approach to asymmetric diamination.

Authors:  Baoguo Zhao; Haifeng Du; Yian Shi
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

9.  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

10.  Site-Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes.

Authors:  James A Law; Noah M Bartfield; James H Frederich
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-19       Impact factor: 16.823
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