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Literature DB >> 20726591

Formal nucleophilic substitution of bromocyclopropanes with amides en route to conformationally constrained β-amino acid derivatives.

Anthony R Prosser¹, Joseph E Banning, Marina Rubina, Michael Rubin.

Abstract

A chemo- and diastereoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides with secondary amides is described. This method allows for convergent and highly selective synthesis of trans-β-aminocyclopropane carboxylic acid derivatives.

Entities: Chemical

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Year: 2010 PMID： 20726591 DOI： 10.1021/ol101228k

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Identifying Amidyl Radicals for Intermolecular C-H Functionalizations.

Authors: Matthew M Tierney; Stefano Crespi; Davide Ravelli; Erik J Alexanian
Journal: J Org Chem Date: 2019-09-06 Impact factor: 4.354

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. A General N-alkylation Platform via Copper Metallaphotoredox and Silyl Radical Activation of Alkyl Halides.

Authors: Nathan W Dow; Albert Cabré; David W C MacMillan
Journal: Chem Date: 2021-06-16 Impact factor: 25.832

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

Formal nucleophilic substitution of bromocyclopropanes with amides en route to conformationally constrained β-amino acid derivatives.

1. Identifying Amidyl Radicals for Intermolecular C-H Functionalizations.

2. Directed nucleophilic addition of phenoxides to cyclopropenes.

3. A General N-alkylation Platform via Copper Metallaphotoredox and Silyl Radical Activation of Alkyl Halides.

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

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

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

7. Direct synthesis of amides from carboxylic acids and amines using B(OCH2CF3)3.