Literature DB >> 33867688

Unusual Kinetic Profiles for Lewis Base-Catalyzed Sulfenocyclization of ortho-Geranylphenols in Hexafluoroisopropyl Alcohol.

Kevin A Robb1, Soumitra V Athavale1, Scott E Denmark1.   

Abstract

The kinetic behavior of the Lewis base-catalyzed sulfenocyclization of polyenes in hexafluoroisopropyl alcohol (HFIP) was explored. The rate of reaction is not dependent on the electronic properties of the terminal nucleophile, suggesting that this capture step is not rate limiting. Additionally, fractional orders were observed for two of the reaction components. This intriguing profile appears unique to the polyene sulfenocyclization reaction and is not merely due to solvent effects.

Entities:  

Keywords:  Lewis base catalysis; cyclization; hexafluoroisopropyl alcohol; kinetics; polyenes; sulfenocyclization

Year:  2019        PMID： 33867688      PMCID： PMC8048132          DOI： 10.1055/s-0039-1690111

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  19 in total

1.  Enantioselective Polyene Cyclization Catalyzed by a Chiral Brønsted Acid.

Authors:  Liwen Fan; Chunyu Han; Xuerong Li; Jiasheng Yao; Zhengning Wang; Chaochao Yao; Weihao Chen; Tao Wang; Junfeng Zhao
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-02       Impact factor: 15.336

2.  Structural, Mechanistic, Spectroscopic, and Preparative Studies on the Lewis Base Catalyzed, Enantioselective Sulfenofunctionalization of Alkenes.

Authors:  Eduard Hartmann; Scott E Denmark
Journal:  Helv Chim Acta       Date:  2017-09-14       Impact factor: 2.164

3.  Enantioselective polyene cyclization via organo-SOMO catalysis.

Authors:  Sebastian Rendler; David W C Macmillan
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

Review 4.  A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

Authors:  Ryan A Yoder; Jeffrey N Johnston
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

5.  Enantioselective thiourea-catalyzed cationic polycyclizations.

Authors:  Robert R Knowles; Song Lin; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

6.  Concerning the mechanism of a nonenzymic biogenetic-like olefinic cyclization.

Authors:  P A Bartlett; J L Brauman; W S Johnson; R A Volkman
Journal:  J Am Chem Soc       Date:  1973-10-31       Impact factor: 15.419

7.  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

8.  Mechanistic, crystallographic, and computational studies on the catalytic, enantioselective sulfenofunctionalization of alkenes.

Authors:  Scott E Denmark; Eduard Hartmann; David J P Kornfilt; Hao Wang
Journal:  Nat Chem       Date:  2014-11-10       Impact factor: 24.427

9.  Gold(I)-catalyzed enantioselective polycyclization reactions.

Authors:  Steven G Sethofer; Timo Mayer; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

10.  Iridium-catalyzed enantioselective polyene cyclization.

Authors:  Michael A Schafroth; David Sarlah; Simon Krautwald; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2012-12-11       Impact factor: 15.419
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