Literature DB >> 17284039

Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons.

Tomoya Miura1, Tatsuro Harumashi, Masahiro Murakami.   

Abstract

[reaction: see text] Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered beta-enamino esters in good yield. An (oxa-pi-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.

Entities:  

Year:  2007        PMID: 17284039     DOI: 10.1021/ol062882y

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


  2 in total

1.  Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents.

Authors:  Venukrishnan Komanduri; Fernando Pedraza; Michael J Krische
Journal:  Adv Synth Catal       Date:  2008-07-07       Impact factor: 5.837

2.  One-pot synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a Et3N-promoted pseudo five-component reaction.

Authors:  Juan Yao; Lanxiang Zhou; Chen Tan; Cunde Wang
Journal:  Mol Divers       Date:  2014-09-26       Impact factor: 2.943

  2 in total

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