Literature DB >> 19199427

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

Rebecca N Loy1, Eric N Jacobsen.   

Abstract

The catalytic enantioselective intramolecular ring-opening of oxetanes with alcohols is catalyzed by (salen)Co(III) complexes. Either a monomeric or oligomeric catalyst can be used successfully in this transformation, providing 3-substituted tetrahydrofurans in both high yield and enantioselectivity. This methodology extends the range of electrophiles that can be activated toward highly enantioselective addition reactions by (salen)metal catalysts to an important new class.

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Year:  2009        PMID： 19199427      PMCID： PMC2765541          DOI： 10.1021/ja809176m

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


  16 in total

1.  Highly active oligomeric (salen)co catalysts for asymmetric epoxide ring-opening reactions.

Authors:  J M Ready; E N Jacobsen
Journal:  J Am Chem Soc       Date:  2001-03-21       Impact factor: 15.419

2.  Design, synthesis, and evaluation of metabolism-based analogues of haloperidol incapable of forming MPP+-like species.

Authors:  M Lyles-Eggleston; R Altundas; J Xia; D M N Sikazwe; P Fan; Q Yang; S Li; W Zhang; X Zhu; A W Schmidt; M Vanase-Frawley; A Shrihkande; A Villalobos; R F Borne; S Y Ablordeppey
Journal:  J Med Chem       Date:  2004-01-29       Impact factor: 7.446

3.  Oxetanes as promising modules in drug discovery.

Authors:  Georg Wuitschik; Mark Rogers-Evans; Klaus Müller; Holger Fischer; Björn Wagner; Franz Schuler; Liudmila Polonchuk; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

4.  Spirocyclic oxetanes: synthesis and properties.

Authors:  Georg Wuitschik; Mark Rogers-Evans; Andreas Buckl; Maurizio Bernasconi; Moritz Märki; Thierry Godel; Holger Fischer; Björn Wagner; Isabelle Parrilla; Franz Schuler; Josef Schneider; André Alker; W Bernd Schweizer; Klaus Müller; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  A practical oligomeric [(salen)Co] catalyst for asymmetric epoxide ring-opening reactions.

Authors:  Joseph M Ready; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2002-04-15       Impact factor: 15.336

6.  Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols.

Authors:  Giuseppe Bartoli; Marcella Bosco; Armando Carlone; Manuela Locatelli; Paolo Melchiorre; Letizia Sambri
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

7.  Synthesis and antiallergy activity of 4-(diarylhydroxymethyl)-1-[3-(aryloxy)propyl]piperidines and structurally related compounds.

Authors:  D A Walsh; S K Franzyshen; J M Yanni
Journal:  J Med Chem       Date:  1989-01       Impact factor: 7.446

8.  A new series of cyclic amino acids as inhibitors of S-adenosyl L-methionine synthetase.

Authors:  K Lavrador; D Guillerm; G Guillerm
Journal:  Bioorg Med Chem Lett       Date:  1998-07-07       Impact factor: 2.823

9.  Mechanistic investigation leads to a synthetic improvement in the hydrolytic kinetic resolution of terminal epoxides.

Authors:  Lars P C Nielsen; Christian P Stevenson; Donna G Blackmond; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2004-02-11       Impact factor: 15.419

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

Authors:  Toshihiko Sone; Gang Lu; Shigeki Matsunaga; Masakatsu Shibasaki
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  19 in total

1.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

2.  Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes.

Authors:  Daniel A Strassfeld; Zachary K Wickens; Elias Picazo; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-05-06       Impact factor: 15.419

3.  Organocatalytic Asymmetric Synthesis of α-Oxetanyl and α-Azetidinyl Tertiary Alkyl Fluorides and Chlorides.

Authors:  Ransheng Ding; Christian Wolf
Journal:  Org Lett       Date:  2018-01-23       Impact factor: 6.005

4.  Mechanistic basis for high reactivity of (salen)Co-OTs in the hydrolytic kinetic resolution of terminal epoxides.

Authors:  Lars P C Nielsen; Stephan J Zuend; David D Ford; Eric N Jacobsen
Journal:  J Org Chem       Date:  2012-02-08       Impact factor: 4.354

5.  A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.

Authors:  David E White; Pamela M Tadross; Zhe Lu; Eric N Jacobsen
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

6.  A practical method for the synthesis of highly enantioenriched trans-1,2-amino alcohols.

Authors:  James A Birrell; Eric N Jacobsen
Journal:  Org Lett       Date:  2013-06-06       Impact factor: 6.005

7.  Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes.

Authors:  Juan J Rojas; Elena Torrisi; Maryne A J Dubois; Riashat Hossain; Andrew J P White; Giovanni Zappia; James J Mousseau; Chulho Choi; James A Bull
Journal:  Org Lett       Date:  2022-03-21       Impact factor: 6.005

8.  Mechanistic basis for high stereoselectivity and broad substrate scope in the (salen)Co(III)-catalyzed hydrolytic kinetic resolution.

Authors:  David D Ford; Lars P C Nielsen; Stephan J Zuend; Charles B Musgrave; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-10-07       Impact factor: 15.419

9.  Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization.

Authors:  Kimberly S Petersen
Journal:  Tetrahedron Lett       Date:  2015-11-25       Impact factor: 2.415

10.  3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular annulation reactions.

Authors:  Zengwei Lai; Renwei Zhang; Qiang Feng; Jianwei Sun
Journal:  Chem Sci       Date:  2020-09-08       Impact factor: 9.825
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