Literature DB >> 15686360

Cinchona alkaloid/sulfinyl chloride combinations: enantioselective sulfinylating agents of alcohols.

Norio Shibata1, Mitsuharu Matsunaga, Masaya Nakagawa, Takeo Fukuzumi, Shuichi Nakamura, Takeshi Toru.   

Abstract

We report a novel approach to asymmetric sulfinylation reactions based on a cinchona alkaloid/sulfinyl chloride combination that acts as the first asymmetric sulfinylating agents of achiral alcohols. Both enantiomers of arenesulfinates are obtained with up to 99% ee. The significantly high enantioselectivity observed in this case could be explained by dynamic kinetic resolution.

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Year:  2005        PMID： 15686360     DOI： 10.1021/ja0430189

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


  5 in total

Review 1.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

2.  Enantioselective sulfonylation reactions mediated by a tetrapeptide catalyst.

Authors:  Kristin Williams Fiori; Angela L A Puchlopek; Scott J Miller
Journal:  Nat Chem       Date:  2009-11       Impact factor: 24.427

3.  K2CO3-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates.

Authors:  Harshita Singh Korawat; Ashok K Basak
Journal:  ACS Omega       Date:  2020-07-08

4.  Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds.

Authors:  Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Chem Rev       Date:  2020-04-29       Impact factor: 60.622

5.  Synthesis of chiral sulfinate esters by asymmetric condensation.

Authors:  Xin Zhang; Esther Cai Xia Ang; Ziqi Yang; Choon Wee Kee; Choon-Hong Tan
Journal:  Nature       Date:  2022-02-14       Impact factor: 69.504
  5 in total

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