Literature DB >> 35119714

Enantioselective Iridium-Catalyzed Reductive Coupling of Dienes with Oxetanones and N-Acyl-Azetidinones Mediated by 2-Propanol.

Cole C Meyer1, Zachary J Dubey1, Michael J Krische1.   

Abstract

Cyclometallated iridium-PhanePhos complexes generated in situ from [Ir(cod)Cl]2 and (R)-PhanePhos catalyze 2-propanol-mediated reductive couplings of 2-substituted dienes with oxetanone and N-acyl-azetidinones to form branched homoallylic oxetanols and azetidinols with excellent control of regio- and enantioselectivity without C-C cleavage of the strained ring via enantiotopic π-facial selection of transient allyliridium nucleophiles. This work represents the first systematic study of enantioselective additions to symmetric ketones.
© 2022 Wiley-VCH GmbH.

Entities:  

Keywords:  Allylation; Bioisostere; Diene; Enantioselective; Iridium

Mesh：

Substances：

Year:  2022        PMID： 35119714      PMCID： PMC8940717          DOI： 10.1002/anie.202115959

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  45 in total

1.  Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones.

Authors:  Scott E Denmark; Jiping Fu
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

Review 2.  Mitigating heterocycle metabolism in drug discovery.

Authors:  David J St Jean; Christopher Fotsch
Journal:  J Med Chem       Date:  2012-05-07       Impact factor: 7.446

3.  Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration.

Authors:  Rauful Alam; Tobias Vollgraff; Lars Eriksson; Kálmán J Szabó
Journal:  J Am Chem Soc       Date:  2015-08-31       Impact factor: 15.419

Review 4.  Oxetanes as versatile elements in drug discovery and synthesis.

Authors:  Johannes A Burkhard; Georg Wuitschik; Mark Rogers-Evans; Klaus Müller; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-22       Impact factor: 15.336

Review 5.  Asymmetric catalysis for the construction of quaternary carbon centres: nucleophilic addition on ketones and ketimines.

Authors:  Olivier Riant; Jérôme Hannedouche
Journal:  Org Biomol Chem       Date:  2007-02-05       Impact factor: 3.876

Review 6.  Four-membered ring-containing spirocycles: synthetic strategies and opportunities.

Authors:  Erick M Carreira; Thomas C Fessard
Journal:  Chem Rev       Date:  2014-07-08       Impact factor: 60.622

7.  The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Authors:  Barry M Trost; Andrew H Weiss
Journal:  Adv Synth Catal       Date:  2009-05       Impact factor: 5.837

Review 8.  Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.

Authors:  Khoa D Nguyen; Boyoung Y Park; Tom Luong; Hiroki Sato; Victoria J Garza; Michael J Krische
Journal:  Science       Date:  2016-10-21       Impact factor: 47.728

9.  CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications.

Authors:  Chengxi Li; Richard Y Liu; Luke T Jesikiewicz; Yang Yang; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-03-12       Impact factor: 15.419

10.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.