Recent trends in organocatalyzed asymmetric reduction of prochiral ketones
The asymmetric reduction of unsaturated carbonyl functionalities is one of the most important chemical transformations to generate optically active stereocenters. Optically active secondary alcohols are a class of compounds which displays significant importance as various intermediates, chiral build...
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| Published in | Catalysis science & technology Vol. 8; no. 4; pp. 955 - 969 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Cambridge
Royal Society of Chemistry
2018
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| Subjects | |
| Online Access | Get full text |
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| Summary: | The asymmetric reduction of unsaturated carbonyl functionalities is one of the most important chemical transformations to generate optically active stereocenters. Optically active secondary alcohols are a class of compounds which displays significant importance as various intermediates, chiral building blocks and biologically active compounds. Various methods have been utilized for the synthesis of these secondary alcohols to achieve high activity and enantioselectivity for reduction reactions of prochiral ketones. Organocatalysis plays a pivotal role in the area of asymmetric synthesis. Recently, several types of organocatalysts have been investigated for asymmetric reduction of prochiral ketones to obtain chiral alcohols with excellent enantioselectivity. This review is focused on selected studies on the development of organocatalysts which are classified into six major categories: i) oxazaborolidine, ii) hydroxyamide, iii) BINOL, iv) ionic liquid, v) phosphoric acid and vi) thiourea-amine based catalysts for asymmetric reduction of prochiral ketones. Mechanistic studies performed in this area are also briefly summarised herein. This review specifically focuses on the most recent applications of organocatalysts used for reduction of ketones for the past seven years.
This review depicts the recent practices followed in organocatalyzed asymmetric reduction of prochiral ketones, highlighting the main organocatalysts used for the past seven years. |
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| Bibliography: | 2 He is also working on nanomaterials, enzymatic catalysis and the use of non-conventional techniques like ultrasound and microwaves for various reactions. etc. Bhalchandra M. Bhanage obtained his doctorate from Pune University in 1996. He spent more than one year at Tohoku University, Japan (1997-1998), and four years at Hokkaido University, Japan (2000-2003) as a postdoctoral fellow with Prof. M. Arai. In 2004, he joined the Institute of Chemical Technology, Mumbai, India as a professor of industrial and engineering chemistry. His current research interest includes developing novel catalytic systems for carbonylation, CO fixation for valuable chemicals, asymmetric hydrogenation of ketones, hydroformylation, various coupling reactions, amination reactions Priya Singh received her M.Sc. degree from the Institute of Chemical Technology in 2017. As a part of the Master's research project that was completed under the guidance of Prof. Shriniwas D. Samant at the Institute of Chemical Technology, Priya was able to develop methodologies for bromination study of dihydroquinolines. She is currently doing internship in DFT studies and computational modeling of organic molecules under Dr. K. Joshi at the Institute of Chemical Technology. Her research interests focus on designing organic molecules with biological activities and transition metal catalyzed asymmetric synthesis. Vaishali S. Shende received her M.Sc. degree in organic chemistry from Pune University in 2009. After working as a Research Associate in Lupin Pharmaceuticals Ltd, India for one year, she joined CSIR-NCL, India in 2011 to pursue her Ph.D. under the supervision of Dr. A. A. Kelkar and Dr. S. Iyer with a CSIR-JRF fellowship received from CSIR-Delhi, India. Her PhD work focused on transition metal catalyzed asymmetric hydrogenation reactions. Then she worked as a Women Scientist in 2016 in CSIR-URDIP, India. In 2017, she joined the group of Prof. B. M. Bhanage as a postdoctoral researcher with a National Postdoctoral Fellowship received from SERB-DST, India. Her current research work includes biomass conversion to chiral platform molecules. |
| ISSN: | 2044-4753 2044-4761 |
| DOI: | 10.1039/c7cy02409f |