Literature DB >> 23193947

Iridium-catalyzed enantioselective polyene cyclization.

Michael A Schafroth1, David Sarlah, Simon Krautwald, Erick M Carreira.   

Abstract

A highly enantioselective polycyclization method has been developed using the combination of Lewis acid activation with iridium-catalyzed allylic substitution. This strategy relies on direct use of branched, racemic allylic alcohols and furnishes a diverse and unique set of carbo- and heteropolycyclic ring systems in good yields and ≥99% ee.

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Year:  2012        PMID： 23193947     DOI： 10.1021/ja310386m

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


  26 in total

Review 1.  Expanding the enzyme universe: accessing non-natural reactions by mechanism-guided directed evolution.

Authors:  Hans Renata; Z Jane Wang; Frances H Arnold
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-03       Impact factor: 15.336

2.  Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-17       Impact factor: 15.336

3.  Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes.

Authors:  Zhonglin Tao; Kevin A Robb; Kuo Zhao; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2018-03-06       Impact factor: 15.419

4.  Cobalt-Catalyzed Hydrogen-Atom Transfer Induces Bicyclizations that Tolerate Electron-Rich and Electron-Deficient Intermediate Alkenes.

Authors:  Darius Vrubliauskas; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-25       Impact factor: 15.336

5.  Construction of vicinal tertiary and all-carbon quaternary stereocenters via Ir-catalyzed regio-, diastereo-, and enantioselective allylic alkylation and applications in sequential Pd catalysis.

Authors:  Wen-Bo Liu; Corey M Reeves; Scott C Virgil; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-07-12       Impact factor: 15.419

6.  A Cyclization/Oxygenation Scheme for the Conversion of Polyenes into C3-Oxygenated Polycycles.

Authors:  Michael J Geier; Michel R Gagné
Journal:  Organometallics       Date:  2013-01-07       Impact factor: 3.876

7.  Catalytic platinum-initiated cation-olefin reactions with alkene terminating groups.

Authors:  Joseph G Sokol; Nikki A Cochrane; Jennifer J Becker; Michel R Gagné
Journal:  Chem Commun (Camb)       Date:  2013-04-26       Impact factor: 6.222

8.  Cation control of diastereoselectivity in iridium-catalyzed allylic substitutions. Formation of enantioenriched tertiary alcohols and thioethers by allylation of 5H-oxazol-4-ones and 5H-thiazol-4-ones.

Authors:  Wenyong Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-12-19       Impact factor: 15.419

9.  Catalytic enantioselective cyclization and C3-fluorination of polyenes.

Authors:  Nikki A Cochrane; Ha Nguyen; Michel R Gagne
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

10.  Iridium-catalyzed enantioselective allylic substitution of unstabilized enolates derived from α,β-unsaturated ketones.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336
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