Literature DB >> 19169459

Recent development and improvement for boron hydride-based catalytic asymmetric reduction of unsymmetrical ketones.

Byung Tae Cho1.   

Abstract

Catalytic asymmetric reduction of prochiral ketones with hydrides such as boranes and borohydrides is one of the simplest and the most convenient methods for obtaining chiral alcohols. This tutorial review describes the most significant advances recently achieved for enhancing the enantioselectivity and practicability of the reduction using this methodology. The review covers the development of new homogeneous and/or immobilized catalysts for asymmetric reduction using borane or borohydride reagents and practical improvement of the well-known oxazaborolidine (OAB)-catalysed reduction through developing more stable, cost effective and recoverable OABs, scalable and environmental friendly borane sources, and one-pot procedures for the reduction.

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Year:  2008        PMID: 19169459     DOI: 10.1039/b811341f

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  14 in total

1.  Synthesis and stability of new spiroaminoborate esters.

Authors:  Viatcheslav Stepanenko; Melvin de Jesús; Carmelo Garcia; Charles L Barnes; Margarita Ortiz-Marciales
Journal:  Tetrahedron Lett       Date:  2012-02-22       Impact factor: 2.415

2.  Kinetic resolution of secondary alcohols using amidine-based catalysts.

Authors:  Ximin Li; Hui Jiang; Eric W Uffman; Lei Guo; Yuhua Zhang; Xing Yang; Vladimir B Birman
Journal:  J Org Chem       Date:  2012-02-09       Impact factor: 4.354

3.  Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.

Authors:  De Run Li; Anyu He; J R Falck
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

4.  Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates.

Authors:  Gary A Molander; Steven R Wisniewski
Journal:  J Am Chem Soc       Date:  2012-10-01       Impact factor: 15.419

5.  Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.

Authors:  Kun Huang; Haiyang Wang; Viatcheslav Stepanenko; Melvin De Jesús; Carilyn Torruellas; Wildeliz Correa; Margarita Ortiz-Marciales
Journal:  J Org Chem       Date:  2011-02-04       Impact factor: 4.354

6.  Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman and thiochroman containing ketones.

Authors:  Viatcheslav Stepanenko; Melvin De Jesús; Wildeliz Correa; Lorianne Bermúdez; Cindybeth Vázquez; Irisbel Guzmán; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2009-12-11

Review 7.  Silver nanomaterials: synthesis and (electro/photo) catalytic applications.

Authors:  Rakesh Kumar Sharma; Sneha Yadav; Sriparna Dutta; Hanumant B Kale; Indrajeet R Warkad; Radek Zbořil; Rajender S Varma; Manoj B Gawande
Journal:  Chem Soc Rev       Date:  2021-10-18       Impact factor: 54.564

8.  Spiroborate ester-mediated asymmetric synthesis of beta-hydroxy ethers and its conversion to highly enantiopure beta-amino ethers.

Authors:  Kun Huang; Margarita Ortiz-Marciales; Wildeliz Correa; Edgardo Pomales; Xaira Y López
Journal:  J Org Chem       Date:  2009-06-05       Impact factor: 4.354

9.  Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.

Authors:  Hai-Yang Wang; Kun Huang; Melvin De Jesús; Sandraliz Espinosa; Luis E Piñero-Santiago; Charles L Barnes; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2016-02-15

10.  A Direct and Stereoretentive Synthesis of Amides from Cyclic Alcohols.

Authors:  Deboprosad Mondal; Luca Bellucci; Salvatore D Lepore
Journal:  European J Org Chem       Date:  2011-12
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