Literature DB >> 17629286

Catalytic stereoselective synthesis of highly substituted indanones via tandem Nazarov cyclization and electrophilic fluorination trapping.

Jing Nie1, Hong-Wei Zhu, Han-Feng Cui, Ming-Qing Hua, Jun-An Ma.   

Abstract

A new catalytic stereoselective tandem transformation via Nazarov cyclization/electrophilic fluorination has been accomplished. This sequence is efficiently catalyzed by a Cu(II) complex to afford fluorine-containing 1-indanone derivatives with two new stereocenters with high diastereoselectivity (trans/cis up to 49/1). Three examples of catalytic enantioselective tandem transformation are presented.

Entities:  

Year:  2007        PMID： 17629286     DOI： 10.1021/ol071114j

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


  14 in total

1.  Neutral Nazarov-type cyclization catalyzed by palladium(0).

Authors:  Naoyuki Shimada; Craig Stewart; William F Bow; Anais Jolit; Kahoano Wong; Zhe Zhou; Marcus A Tius
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  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

3.  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

4.  Asymmetric Nazarov Cyclizations.

Authors:  Naoyuki Shimada; Craig Stewart; Marcus A Tius
Journal:  Tetrahedron       Date:  2011-08-19       Impact factor: 2.457

5.  Enantioselective Nazarov Cyclization Catalyzed by a Cinchona Alkaloid Derivative.

Authors:  Yu-Wen Huang; Alison J Frontier
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

Review 6.  Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

Authors:  Yi Zhu; Jianlin Han; Jiandong Wang; Norio Shibata; Mikiko Sodeoka; Vadim A Soloshonok; Jaime A S Coelho; F Dean Toste
Journal:  Chem Rev       Date:  2018-04-02       Impact factor: 60.622

7.  Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.

Authors:  William F Bow; Ashok K Basak; Anais Jolit; David A Vicic; Marcus A Tius
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

8.  Catalytic Intramolecular Aminofluorination, Oxyfluorination, and Carbofluorination with a Stable and Versatile Hypervalent Fluoroiodine Reagent.

Authors:  Weiming Yuan; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-09       Impact factor: 15.336

9.  A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis.

Authors:  Zhonglin Liu; Lucas J Oxtoby; Mingyu Liu; Zi-Qi Li; Van T Tran; Yang Gao; Keary M Engle
Journal:  J Am Chem Soc       Date:  2021-06-02       Impact factor: 16.383

10.  Salen promoted enantioselective Nazarov cyclizations of activated and unactivated dienones.

Authors:  Gerri E Hutson; Yunus E Türkmen; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2013-03-25       Impact factor: 15.419
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