Literature DB >> 26068952

Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene O-H Insertion Reaction.

Simon M Nicolle1, William Lewis1, Christopher J Hayes1, Christopher J Moody2.   

Abstract

Copper- or rhodium-catalyzed reactions of diazocarbonyl compounds with β-hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single-step process starts as a carbene O-H insertion reaction, but is diverted by an intramolecular aldol reaction.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aldol reaction; carbenes; diazo compounds; tetrahydrofurans; transition-metal catalysis

Mesh：

Substances：

Year:  2015        PMID： 26068952     DOI： 10.1002/anie.201502484

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


  4 in total

Review 1.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

2.  Asymmetric synthesis of isochromanone derivatives via trapping carboxylic oxonium ylides and aldol cascade.

Authors:  Jiawen Lang; Siyuan Wang; Changli He; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2021-12-27       Impact factor: 9.825

3.  Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones.

Authors:  Weida Liang; Xinpei Cai; Mingji Dai
Journal:  Chem Sci       Date:  2020-11-20       Impact factor: 9.825

Review 4.  Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds.

Authors:  Daniil Zhukovsky; Dmitry Dar'in; Olga Bakulina; Mikhail Krasavin
Journal:  Molecules       Date:  2022-03-21       Impact factor: 4.411
  4 in total

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