Literature DB >> 15113194

Cinchona alkaloid-lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions.

Cheng Zhu1, Xiaoqiang Shen, Scott G Nelson.   

Abstract

Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted beta-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized by the operational simplicity derived from using commercially available or easily obtained (one-step) reaction catalysts and in situ ketene generation from acid chlorides. The range of aldehyde substrates that serve as effective AAC substrates include sterically hindered aldehydes such as cyclohexanecarboxaldehyde and pivaldehyde.

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Year:  2004        PMID： 15113194     DOI： 10.1021/ja0492900

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


  21 in total

1.  From bifunctional to trifunctional (tricomponent nucleophile-transition metal-lewis acid) catalysis: the catalytic, enantioselective α-fluorination of acid chlorides.

Authors:  Jeremy Erb; Daniel H Paull; Travis Dudding; Lee Belding; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  Rapid and stereochemically flexible synthesis of polypropionates: super-silyl-governed aldol cascades.

Authors:  Patrick B Brady; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-17       Impact factor: 15.336

3.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

4.  Total synthesis of theopederin D.

Authors:  Michael E Green; Jason C Rech; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Simple β-lactones are potent irreversible antagonists for strigolactone receptors.

Authors:  Haibo Xiang; Ruifeng Yao; Tianfei Quan; Fei Wang; Li Chen; Xiaoxi Du; Wenhao Zhang; Haiteng Deng; Daoxin Xie; Tuoping Luo
Journal:  Cell Res       Date:  2017-08-18       Impact factor: 25.617

6.  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

7.  Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2010-11-18       Impact factor: 15.419

8.  Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Authors:  Tyler M Rohrs; Qi Qin; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-28       Impact factor: 15.336

9.  Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  Org Lett       Date:  2011-05-17       Impact factor: 6.005

10.  Bifunctional asymmetric catalysis: cooperative Lewis acid/base systems.

Authors:  Daniel H Paull; Ciby J Abraham; Michael T Scerba; Ethan Alden-Danforth; Thomas Lectka
Journal:  Acc Chem Res       Date:  2008-04-11       Impact factor: 22.384
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