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Literature DB >> 22700327

Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Daniel T Cohen¹, Chad C Eichman, Eric M Phillips, Emily R Zarefsky, Karl A Scheidt.

Abstract

New DKR type: An N-heterocyclic carbene (NHC)-catalyzed dynamic kinetic resolution of racemic α-substituted β-keto esters has been developed. This method relies on the epimerization of an NHC-enol intermediate before subsequent aldol/acylation events. Highly substituted β-lactones are produced in good yield with good to excellent selectivities (see scheme).

Entities: Chemical Disease Gene

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Year: 2012 PMID： 22700327 PMCID： PMC3489928 DOI： 10.1002/anie.201203382

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

64 in total

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2. The catalytic asymmetric Knoevenagel condensation.

Authors: Anna Lee; Anna Michrowska; Sarah Sulzer-Mosse; Benjamin List
Journal: Angew Chem Int Ed Engl Date: 2011-01-20 Impact factor: 15.336

3. Catalytic asymmetric synthesis of complex polypropionates: Lewis base catalyzed aldol equivalents in the synthesis of erythronolide B.

Authors: Binita Chandra; Dezhi Fu; Scott G Nelson
Journal: Angew Chem Int Ed Engl Date: 2010-03-29 Impact factor: 15.336

4. Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes.

Authors: Brooks E Maki; Audrey Chan; Eric M Phillips; Karl A Scheidt
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

5. Catalytic kinetic resolution of cyclic secondary amines.

Authors: Michael Binanzer; Sheng-Ying Hsieh; Jeffrey W Bode
Journal: J Am Chem Soc Date: 2011-11-18 Impact factor: 15.419

6. N-heterocyclic carbene-catalyzed enantioselective Mannich reactions with alpha-aryloxyacetaldehydes.

Authors: Yasufumi Kawanaka; Eric M Phillips; Karl A Scheidt
Journal: J Am Chem Soc Date: 2009-12-23 Impact factor: 15.419

7. Dynamic kinetic resolution and desymmetrization of enantiotopic groups by cyclodehydration of racemic or prochiral delta-oxoesters with (R)-phenylglycinol: enantioselective synthesis of piperidines.

Authors: Mercedes Amat; Margalida Cantó; Núria Llor; Viviana Ponzo; Maria Pérez; Joan Bosch
Journal: Angew Chem Int Ed Engl Date: 2002-01-18 Impact factor: 15.336

8. Catalytic enantioselective synthesis of sulfinate esters through the dynamic resolution of tert-butanesulfinyl chloride.

Authors: Jared W Evans; Matthew B Fierman; Scott J Miller; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2004-07-07 Impact factor: 15.419

9. Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors: Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal: J Am Chem Soc Date: 2007-07-31 Impact factor: 15.419

10. Impact of solvent polarity on N-heterocyclic carbene-catalyzed beta-protonations of homoenolate equivalents.

Authors: Brooks E Maki; Eric V Patterson; Christopher J Cramer; Karl A Scheidt
Journal: Org Lett Date: 2009-09-03 Impact factor: 6.005

12 in total

1. Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions.

Authors: Samuel L Bartlett; Jeffrey S Johnson
Journal: Acc Chem Res Date: 2017-08-17 Impact factor: 22.384

2. Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors: Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal: Chem Sci Date: 2014-05-01 Impact factor: 9.825

3. Direct Zinc(II)-Catalyzed Enantioconvergent Additions of Terminal Alkynes to α-Keto Esters.

Authors: Blane P Zavesky; Jeffrey S Johnson
Journal: Angew Chem Int Ed Engl Date: 2017-06-20 Impact factor: 15.336

4. Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.

Authors: Samuel L Bartlett; Kimberly M Keiter; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2017-03-02 Impact factor: 15.419

5. Stereoconvergent Conjugate Addition of Arylboronic Acids to α-Angelica Lactone Derivatives: Synthesis of Stereochemically Complex γ-Butyrolactones.

Authors: Jessica A Griswold; Jeffrey S Johnson
Journal: ACS Catal Date: 2019-11-19 Impact factor: 13.084

6. Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application.

Authors: Daniel T Cohen; Ryne C Johnston; Nicholas T Rosson; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-14 Impact factor: 6.222

7. Asymmetric Synthesis of β-Amino Amides by Catalytic Enantioconvergent 2-Aza-Cope Rearrangement.

Authors: C Guy Goodman; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2015-11-12 Impact factor: 15.419

8. Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile.

Authors: Pedro De Jesús Cruz; Evan T Crawford; Shubin Liu; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2021-09-27 Impact factor: 16.383

9. NHC-Catalyzed Asymmetric Synthesis of Functionalized Succinimides from Enals and α-Ketoamides.

Authors: Lei Wang; Qijian Ni; Marcus Blümel; Tao Shu; Gerhard Raabe; Dieter Enders
Journal: Chemistry Date: 2015-04-15 Impact factor: 5.236

10. Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.

Authors: C Guy Goodman; Morgan M Walker; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2014-12-23 Impact factor: 15.419