Literature DB >> 23845068

Formal substitution of bromocyclopropanes with nitrogen nucleophiles.

Joseph E Banning1, Jacob Gentillon, Pavel G Ryabchuk, Anthony R Prosser, Andrew Rogers, Andrew Edwards, Andrew Holtzen, Ivan A Babkov, Marina Rubina, Michael Rubin.   

Abstract

A highly chemo- and diastereoselective protocol toward amino-substituted donor-acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochemically defined and densely functionalized cyclopropylamine derivatives.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23845068     DOI： 10.1021/jo4011798

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


  6 in total

1.  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

2.  Efficient one-pot synthesis of 1-arylcycloprop-2-ene-1-carboxamides.

Authors:  Andrew Edwards; Michael Rubin
Journal:  Org Biomol Chem       Date:  2016-03-14       Impact factor: 3.876

3.  Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates.

Authors:  Vladimir A Maslivetc; Liliya V Frolova; Snezna Rogelj; Anna A Maslivetc; Marina Rubina; Michael Rubin
Journal:  J Org Chem       Date:  2018-10-30       Impact factor: 4.354

4.  Synthesis of 1,5-Dioxocanes via the Two-Fold C-O Bond Forming Nucleophilic 4+4-Cyclodimerization of Cycloprop-2-en-1-ylmethanols.

Authors:  Andrew Edwards; Trevor Bennin; Marina Rubina; Michael Rubin
Journal:  RSC Adv       Date:  2015-08-19       Impact factor: 3.361

5.  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

6.  One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes.

Authors:  Vladimir A Maslivetc; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2015-08-05       Impact factor: 3.876
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.