Literature DB >> 32352184

Enantioselective S-H Insertion Reactions of α-Carbonyl Sulfoxonium Ylides.

Patrícia B Momo1, Alexandria N Leveille2, Elliot H E Farrar3, Matthew N Grayson3, Anita E Mattson2, Antonio C B Burtoloso1.   

Abstract

The first example of enantioselective S-H insertion reactions of sulfoxonium ylides is reported. Under the influence of thiourea catalysis, excellent levels of enantiocontrol (up to 95 % ee) and yields (up to 97 %) are achieved for 31 examples in S-H insertion reactions of aryl thiols and α-carbonyl sulfoxonium ylides.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  S−H insertion; aryl thiol; enantioselectivity; organocatalysis; sulfoxonium ylide

Year:  2020        PMID： 32352184     DOI： 10.1002/anie.202005563

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


  7 in total

1.  Insights into the Activation Mode of α-Carbonyl Sulfoxonium Ylides in Rhodium-Catalyzed C-H Activation: A Theoretical Study.

Authors:  Dianmin Zhang; Xiaofang He; Tao Yang; Song Liu
Journal:  ChemistryOpen       Date:  2022-02-24       Impact factor: 2.630

2.  Metal-catalyzed B-H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums.

Authors:  Hou-Ji Cao; Xing Wei; Fangxiang Sun; Xiaolei Zhang; Changsheng Lu; Hong Yan
Journal:  Chem Sci       Date:  2021-11-19       Impact factor: 9.825

Review 3.  Asymmetric transformations from sulfoxonium ylides.

Authors:  Clarice A D Caiuby; Lucas G Furniel; Antonio C B Burtoloso
Journal:  Chem Sci       Date:  2021-12-08       Impact factor: 9.825

4.  Comparing the Performances of Force Fields in Conformational Searching of Hydrogen-Bond-Donating Catalysts.

Authors:  Toby Lewis-Atwell; Piers A Townsend; Matthew N Grayson
Journal:  J Org Chem       Date:  2022-04-27       Impact factor: 4.198

5.  Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures.

Authors:  Giorgiana Denisa Bisag; Pietro Pecchini; Michele Mancinelli; Mariafrancesca Fochi; Luca Bernardi
Journal:  Org Lett       Date:  2022-07-20       Impact factor: 6.072

6.  Noncovalent Interactions in the Oxazaborolidine-Catalyzed Enantioselective Mukaiyama Aldol.

Authors:  Elliot H E Farrar; Matthew N Grayson
Journal:  J Org Chem       Date:  2022-07-18       Impact factor: 4.198

7.  A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.

Authors:  Daniel A Strassfeld; Russell F Algera; Zachary K Wickens; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2021-06-21       Impact factor: 16.383
  7 in total

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