Literature DB >> 16620081

Tandem Nazarov cyclization-michael addition sequence catalyzed by an Ir(III) complex.

Mesfin Janka1, Wei He, Inga E Haedicke, Frank R Fronczek, Alison J Frontier, Richard Eisenberg.   

Abstract

The first examples of a tandem Nazarov cyclization/Michael addition process are described. The sequence is efficiently catalyzed by Ir[Me(CO)(dppe)(DIB)]2+ and occurs with high diastereoselectivity, creating three contiguous stereocenters. The mechanistic factors controlling the reactivity and diastereoselectivity are discussed.

Entities:  

Year:  2006        PMID： 16620081     DOI： 10.1021/ja058772o

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

1.  Intramolecular azide trapping of the Nazarov intermediate: formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation.

Authors:  Ali Rostami; Yong Wang; Atta M Arif; Robert McDonald; F G West
Journal:  Org Lett       Date:  2007-01-26       Impact factor: 6.005

2.  Design of chiral auxiliaries for the allene ether nazarov cyclization.

Authors:  April R Banaag; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2007-04-11       Impact factor: 15.419

Review 3.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

4.  A highly reactive dicationic iridium(III) catalyst for the polarized Nazarov cyclization reaction.

Authors:  Tulaza Vaidya; Abdurrahman C Atesin; Ildiko R Herrick; Alison J Frontier; Richard Eisenberg
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-26       Impact factor: 15.336

5.  Traceless chiral auxiliaries for the allene ether Nazarov cyclization.

Authors:  April R Banaag; Marcus A Tius
Journal:  J Org Chem       Date:  2008-09-23       Impact factor: 4.354

6.  Efficient Nazarov cyclization/Wagner-Meerwein rearrangement terminated by a Cu(II)-promoted oxidation: synthesis of 4-alkylidene cyclopentenones.

Authors:  David Lebœuf; Eric Theiste; Vincent Gandon; Stephanie L Daifuku; Michael L Neidig; Alison J Frontier
Journal:  Chemistry       Date:  2013-02-21       Impact factor: 5.236

7.  Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

Authors:  David Lebœuf; Vincent Gandon; Jennifer Ciesielski; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2012-04-03       Impact factor: 15.419

8.  Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Authors:  Jie Huang; David Lebœuf; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-04-05       Impact factor: 15.419

9.  Conjugate addition-initiated Nazarov cyclization.

Authors:  Joshua L Brooks; Patrick A Caruana; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

10.  Interrupting the Nazarov cyclization with indoles.

Authors:  Ashok K Basak; Marcus A Tius
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005
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