Literature DB >> 19165848

Catalytic asymmetric synthesis of 2,2-disubstituted oxetanes from ketones by using a one-pot sequential addition of sulfur ylide.

Toshihiko Sone1, Gang Lu, Shigeki Matsunaga, Masakatsu Shibasaki.   

Abstract

Better the second time around: The title compounds were synthesized by using a one-pot double methylene transfer catalyzed by a heterobimetallic La/Li complex. Chiral amplification in the second step was the key to obtaining oxetanes in high enantiomeric excess (see scheme).

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Year:  2009        PMID： 19165848     DOI： 10.1002/anie.200805473

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


  5 in total

1.  Enantioselective intramolecular openings of oxetanes catalyzed by (salen)Co(III) complexes: access to enantioenriched tetrahydrofurans.

Authors:  Rebecca N Loy; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

2.  Synthesis of di-, tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization.

Authors:  Owen A Davis; James A Bull
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-14       Impact factor: 15.336

3.  Asymmetric synthesis of 2-substituted oxetan-3-ones via metalated SAMP/RAMP hydrazones.

Authors:  Joanna V Geden; Benjamin O Beasley; Guy J Clarkson; Michael Shipman
Journal:  J Org Chem       Date:  2013-11-11       Impact factor: 4.354

4.  Enantioselective synthesis of 2,2-disubstituted terminal epoxides via catalytic asymmetric Corey-Chaykovsky epoxidation of ketones.

Authors:  Toshihiko Sone; Akitake Yamaguchi; Shigeki Matsunaga; Masakatsu Shibasaki
Journal:  Molecules       Date:  2012-02-07       Impact factor: 4.411

Review 5.  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
  5 in total

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