Literature DB >> 22545651

Chiral phosphoric acid-catalyzed enantioselective and diastereoselective spiroketalizations.

Zhankui Sun1, Grace A Winschel, Alina Borovika, Pavel Nagorny.   

Abstract

Catalytic enantioselective and diastereoselective spiroketalizations with BINOL-derived chiral phosphoric acids are reported. The chiral catalyst can override the inherent preference for the formation of thermodynamic spiroketals, and highly selective formation of nonthermodynamic spiroketals could be achieved under the reaction conditions.

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Year:  2012        PMID: 22545651     DOI: 10.1021/ja302704m

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


  19 in total

1.  Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.

Authors:  Souvagya Biswas; Koji Kubota; Manuel Orlandi; Mathias Turberg; Dillon H Miles; Matthew S Sigman; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-12       Impact factor: 15.336

2.  Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Authors:  Weiwei Zi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

3.  A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis.

Authors:  Vince M Lombardo; Christopher D Thomas; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336

4.  Stereocontrolled cyanohydrin ether synthesis through chiral Brønsted acid-mediated vinyl ether hydrocyanation.

Authors:  Chunliang Lu; Xiaoge Su; Paul E Floreancig
Journal:  J Org Chem       Date:  2013-09-04       Impact factor: 4.354

5.  Stereoselective synthesis of acortatarins A and B.

Authors:  Jacqueline M Wurst; Alyssa L Verano; Derek S Tan
Journal:  Org Lett       Date:  2012-08-27       Impact factor: 6.005

Review 6.  A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

Authors:  Luis Bohé; David Crich
Journal:  Carbohydr Res       Date:  2014-07-01       Impact factor: 2.104

7.  Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.

Authors:  Yubo Cui; Louis A Villafane; Dane J Clausen; Paul E Floreancig
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

8.  Experimental and Computational Studies on Regiodivergent Chiral Phosphoric Acid Catalyzed Cycloisomerization of Mupirocin Methyl Ester.

Authors:  Sibin Wang; Alonso J Arguelles; Jia-Hui Tay; Miyuki Hotta; Paul M Zimmerman; Pavel Nagorny
Journal:  Chemistry       Date:  2020-03-18       Impact factor: 5.236

9.  A Cooperative Hydrogen Bond Donor-Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.

Authors:  Mark A Maskeri; Matthew J O'Connor; Ashley A Jaworski; Anna V Bay; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-27       Impact factor: 15.336

10.  Synthetic, Mechanistic, and Biological Interrogation of Ginkgo biloba Chemical Space En Route to (-)-Bilobalide.

Authors:  Robert M Demoret; Meghan A Baker; Masaki Ohtawa; Shuming Chen; Ching Ching Lam; Sophia Khom; Marisa Roberto; Stefano Forli; Kendall N Houk; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2020-10-16       Impact factor: 15.419

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