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Literature DB >> 24123751

Chiral phosphoric acid directed regioselective acetalization of carbohydrate-derived 1,2-diols.

Enoch Mensah¹, Nicole Camasso, Will Kaplan, Pavel Nagorny.

Abstract

In control: A chiral phosphoric acid catalyst significantly enhances or completely overrides the inherent regioselective acetalization profiles exhibited by monosaccharide-derived 1,2-diol substrates. This study represents the first example of chiral-catalyst-directed regio- and enantioselective intermolecular acetalizations, which are complementary to existing methods for substrate-controlled functionalization of polyols.

Entities: Chemical

Keywords: carbohydrates; organocatalysis; protecting groups; regioselectivity; synthetic methods

Mesh：

Substances：

Year: 2013 PMID： 24123751 DOI： 10.1002/anie.201304298

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

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Cited

7 in total

1. Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.

Authors: Jia-Hui Tay; Alonso J Argüelles; Matthew D DeMars; Paul M Zimmerman; David H Sherman; Pavel Nagorny
Journal: J Am Chem Soc Date: 2017-06-19 Impact factor: 15.419

2. Site-Selective and Stereoselective O-Alkylation of Glycosides by Rh(II)-Catalyzed Carbenoid Insertion.

Authors: Jicheng Wu; Xiaolei Li; Xiaotian Qi; Xiyan Duan; Weston L Cracraft; Ilia A Guzei; Peng Liu; Weiping Tang
Journal: J Am Chem Soc Date: 2019-12-03 Impact factor: 15.419

3. Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides.

Authors: Sibin Wang; Oleksii Zhelavskyi; Jeonghyo Lee; Alonso J Argüelles; Yaroslav Ya Khomutnyk; Enoch Mensah; Hao Guo; Rami Hourani; Paul M Zimmerman; Pavel Nagorny
Journal: J Am Chem Soc Date: 2021-10-27 Impact factor: 15.419

4. 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

Chiral phosphoric acid directed regioselective acetalization of carbohydrate-derived 1,2-diols.

1. Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.

2. Site-Selective and Stereoselective O-Alkylation of Glycosides by Rh(II)-Catalyzed Carbenoid Insertion.

3. Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides.

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

5. Sugar Silanes: Versatile Reagents for Stereocontrolled Glycosylation via Intramolecular Aglycone Delivery.

6. Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis.

7. Site-Selective Acylations with Tailor-Made Catalysts.