Literature DB >> 18213988

Recent advances in the semi-pinacol rearrangement of alpha-hydroxy epoxides and related compounds.

Timothy J Snape1.   

Abstract

The semi-pinacol rearrangement is fast becoming an extremely reliable reaction in organic synthesis allowing the rapid construction of relatively complex stereodefined products in high yield. Recent advances in asymmetric synthesis have also enabled enantiopure precursors to partake in the rearrangement showing that extremely high levels of stereospecificity are observed. In this critical review recent advances in the semi-pinacol rearrangement over the past 15 years are examined which demonstrate the extremely high utility of this reaction towards the development of structurally diverse organic building blocks (74 references).

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Year:  2007        PMID: 18213988     DOI: 10.1039/b709634h

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  11 in total

1.  Asymmetric synthesis of D-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy)acetaldehyde.

Authors:  Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal:  J Org Chem       Date:  2010-07-02       Impact factor: 4.354

2.  Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Authors:  Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

3.  Computational elucidation of the origins of reactivity and selectivity in non-aldol aldol rearrangements of cyclic epoxides.

Authors:  Hao Wang; K N Houk; Damian A Allen; Michael E Jung
Journal:  Org Lett       Date:  2011-05-13       Impact factor: 6.005

4.  Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from β-nitro styryl azides.

Authors:  Benjamin J Stokes; Sheng Liu; Tom G Driver
Journal:  J Am Chem Soc       Date:  2011-03-14       Impact factor: 15.419

5.  Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols.

Authors:  Yu Liu; Kanwarpal Bakshi; Peter Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

6.  Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates.

Authors:  Xichen Xu; Yu Qian; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

7.  Enantioselective Aryl-Iodide-Catalyzed Wagner-Meerwein Rearrangements.

Authors:  Hayden A Sharma; Katrina M Mennie; Eugene E Kwan; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-09-03       Impact factor: 15.419

8.  Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts.

Authors:  Bao-Sheng Li; Yuhuang Wang; Zhichao Jin; Yonggui Robin Chi
Journal:  Chem Sci       Date:  2015-07-20       Impact factor: 9.825

9.  Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles.

Authors:  Kai Liu; Guangyang Xu; Jiangtao Sun
Journal:  Chem Sci       Date:  2017-11-06       Impact factor: 9.825

10.  9-Membered Carbocycles: Strategies and Tactics for their Synthesis.

Authors:  Tatjana Huber; Raphael E Wildermuth; Thomas Magauer
Journal:  Chemistry       Date:  2018-03-13       Impact factor: 5.236

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