Literature DB >> 27787993

Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.

Yongho Park1, Corinna S Schindler1, Eric N Jacobsen1.   

Abstract

An enantioselective, catalytic aza-Sakurai cyclization of chlorolactams has been developed as an efficient entry into indolizidine and quinolizidine frameworks. Structure-enantioselectivity relationship studies and mechanistic analysis point to a dual role of the catalyst wherein the thiourea moiety of the catalyst is engaged in both anion binding and Lewis base activation of a substrate.

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Year:  2016        PMID： 27787993      PMCID： PMC5148636          DOI： 10.1021/jacs.6b09736

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


  42 in total

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Authors:  Heilam Wong; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  Highly enantioselective catalytic acyl-pictet-spengler reactions.

Authors:  Mark S Taylor; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2004-09-01       Impact factor: 15.419

3.  Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding.

Authors:  Izzat T Raheem; Parvinder S Thiara; Emily A Peterson; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2007-10-17       Impact factor: 15.419

4.  Catalytic, enantioselective, and highly chemoselective bromocyclization of olefinic dicarbonyl compounds.

Authors:  Yi Zhao; Xiaojian Jiang; Ying-Yeung Yeung
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-14       Impact factor: 15.336

5.  Bioinspired and concise synthesis of (±)-stemoamide.

Authors:  Yan Wang; Lili Zhu; Yuying Zhang; Ran Hong
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-17       Impact factor: 15.336

6.  Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions.

Authors:  Amanda C Cutter; Iain R Miller; John F Keily; Richard K Bellingham; Mark E Light; Richard C D Brown
Journal:  Org Lett       Date:  2011-07-11       Impact factor: 6.005

Review 7.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

8.  Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts.

Authors:  Ling Zhou; Jie Chen; Chong Kiat Tan; Ying-Yeung Yeung
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

9.  Synthesis of alkaloid (-)-205B via stereoselective reductive cross-coupling and intramolecular [3+2] cycloaddition.

Authors:  Dexi Yang; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2012-09-07       Impact factor: 15.419

10.  Enantioselective selenocyclization via dynamic kinetic resolution of seleniranium ions by hydrogen-bond donor catalysts.

Authors:  Hu Zhang; Song Lin; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2014-11-12       Impact factor: 15.419
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  2 in total

1.  Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling.

Authors:  Julie L Hofstra; Alan H Cherney; Ciara M Ordner; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-12-20       Impact factor: 15.419

2.  Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors:  Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419
  2 in total

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