Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations

The catalytic enantioselective ketimine Mannich and its related reactions provide direct access to chiral building blocks bearing an α-tertiary amine stereogenic center, a ubiquitous structural motif in nature. Although ketimines are often viewed as challenging electrophiles, various approaches/stra...

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Main Authors:	Changgong Xu, Carlyn Reep, Jamielyn Jarvis, Brandon Naumann, Burjor Captain, Norito Takenaka
Format:	Article
Language:	English
Published:	MDPI AG 2021-06-01
Series:	Catalysts
Subjects:	ketimine Mannich ketimine allylation aza-Morita–Baylis–Hillman asymmetric catalysis α-tertiary amine β-amino carbonyl
Online Access:	https://www.mdpi.com/2073-4344/11/6/712

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spelling	doaj-5ac09f1c381a487ca0bc0db00ea1faa12021-06-30T23:29:26ZengMDPI AGCatalysts2073-43442021-06-011171271210.3390/catal11060712Asymmetric Catalytic Ketimine Mannich Reactions and Related TransformationsChanggong Xu0Carlyn Reep1Jamielyn Jarvis2Brandon Naumann3Burjor Captain4Norito Takenaka5Chemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901-6975, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901-6975, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901-6975, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901-6975, USADepartment of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33146-0431, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901-6975, USAThe catalytic enantioselective ketimine Mannich and its related reactions provide direct access to chiral building blocks bearing an α-tertiary amine stereogenic center, a ubiquitous structural motif in nature. Although ketimines are often viewed as challenging electrophiles, various approaches/strategies to circumvent or overcome the adverse properties of ketimines have been developed for these transformations. This review showcases the selected examples that highlight the benefits and utilities of various ketimines and remaining challenges associated with them in the context of Mannich, allylation, and aza-Morita–Baylis–Hillman reactions as well as their variants.https://www.mdpi.com/2073-4344/11/6/712ketimine Mannichketimine allylationaza-Morita–Baylis–Hillmanasymmetric catalysisα-tertiary amineβ-amino carbonyl
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Changgong Xu Carlyn Reep Jamielyn Jarvis Brandon Naumann Burjor Captain Norito Takenaka
spellingShingle	Changgong Xu Carlyn Reep Jamielyn Jarvis Brandon Naumann Burjor Captain Norito Takenaka Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations Catalysts ketimine Mannich ketimine allylation aza-Morita–Baylis–Hillman asymmetric catalysis α-tertiary amine β-amino carbonyl
author_facet	Changgong Xu Carlyn Reep Jamielyn Jarvis Brandon Naumann Burjor Captain Norito Takenaka
author_sort	Changgong Xu
title	Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations
title_short	Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations
title_full	Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations
title_fullStr	Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations
title_full_unstemmed	Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations
title_sort	asymmetric catalytic ketimine mannich reactions and related transformations
publisher	MDPI AG
series	Catalysts
issn	2073-4344
publishDate	2021-06-01
description	The catalytic enantioselective ketimine Mannich and its related reactions provide direct access to chiral building blocks bearing an α-tertiary amine stereogenic center, a ubiquitous structural motif in nature. Although ketimines are often viewed as challenging electrophiles, various approaches/strategies to circumvent or overcome the adverse properties of ketimines have been developed for these transformations. This review showcases the selected examples that highlight the benefits and utilities of various ketimines and remaining challenges associated with them in the context of Mannich, allylation, and aza-Morita–Baylis–Hillman reactions as well as their variants.
topic	ketimine Mannich ketimine allylation aza-Morita–Baylis–Hillman asymmetric catalysis α-tertiary amine β-amino carbonyl
url	https://www.mdpi.com/2073-4344/11/6/712
work_keys_str_mv	AT changgongxu asymmetriccatalyticketiminemannichreactionsandrelatedtransformations AT carlynreep asymmetriccatalyticketiminemannichreactionsandrelatedtransformations AT jamielynjarvis asymmetriccatalyticketiminemannichreactionsandrelatedtransformations AT brandonnaumann asymmetriccatalyticketiminemannichreactionsandrelatedtransformations AT burjorcaptain asymmetriccatalyticketiminemannichreactionsandrelatedtransformations AT noritotakenaka asymmetriccatalyticketiminemannichreactionsandrelatedtransformations
_version_	1721351220652670976

Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations

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