Multicomponent Cyclizative 1,2‐Rearrangement Enabled Enantioselective Construction of 2,2‐Disubstituted Pyrrolinones

The 1,2‐rearrangement reaction is one of the most important approaches to construct carbon‐carbon bonds in organic synthesis. However, the development of catalytic asymmetric 1,2‐rearrangements is still far from mature and often suffers from problems such as complex substrates, single product struct...

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Vydáno v:	Angewandte Chemie International Edition Ročník 63; číslo 7; s. e202317182 - n/a
Hlavní autoři:	Li, Xing‐Zi, He, Yu‐Ping, Wu, Hua
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	WEINHEIM Wiley 12.02.2024 Wiley Subscription Services, Inc
Vydání:	International ed. in English
Témata:	1,2-Rearrangement Aldehydes Amines Asymmetry Benzilic acid Carbon Chemical synthesis Chemistry Chemistry, Multidisciplinary Enantiomers Multicomponent Reaction Organocatalysis Physical Sciences Pyrrolinones Quaternary Stereocenter Science & Technology Substrates MIGRATION ALDEHYDE Pyrrolinones Multicomponent Reaction VICINAL TRICARBONYLS Organocatalysis Quaternary Stereocenter 1,2-Rearrangement AMINES BENZILIC ACID REARRANGEMENTS CHEMISTRY SUBSTITUTED PYRROLIN-4-ONES EFFICIENT ACCESS quaternary stereocenter pyrrolinones multicomponent reaction 1,2-rearrangement
ISSN:	1433-7851, 1521-3773, 1521-3773
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Abstract	The 1,2‐rearrangement reaction is one of the most important approaches to construct carbon‐carbon bonds in organic synthesis. However, the development of catalytic asymmetric 1,2‐rearrangements is still far from mature and often suffers from problems such as complex substrates, single product structure, and lack of synthetic application. Multicomponent reaction has been recognized as a robust tool for the synthesis of diverse and tunable products from readily available starting material. Conceptionally and practically, the development of multicomponent asymmetric 1,2‐rearrangements is highly desirable. In this regard, we report herein a three‐component benzilic acid‐type rearrangement of 2,3‐diketoesters, aromatic amines and aldehydes for the asymmetric construction of synthetically challenging pyrrolinones bearing aza‐quaternary stereocenters. To the best of our knowledge, this reaction represents the first example of organocatalyzed multicomponent asymmetric 1,2‐rearrangements. The first organocatalyzed multicomponent asymmetric 1,2‐rearrangement is established, which provides a straightforward access to 2,2‐disubstituted pyrrolinones in excellent chemo‐ and stereoselectivities. This reaction also represents the first example of asymmetric catalytic construction of chiral pyrrolinones bearing aza‐quaternary stereocenters.
AbstractList	The 1,2-rearrangement reaction is one of the most important approaches to construct carbon-carbon bonds in organic synthesis. However, the development of catalytic asymmetric 1,2-rearrangements is still far from mature and often suffers from problems such as complex substrates, single product structure, and lack of synthetic application. Multicomponent reaction has been recognized as a robust tool for the synthesis of diverse and tunable products from readily available starting material. Conceptionally and practically, the development of multicomponent asymmetric 1,2-rearrangements is highly desirable. In this regard, we report herein a three-component benzilic acid-type rearrangement of 2,3-diketoesters, aromatic amines and aldehydes for the asymmetric construction of synthetically challenging pyrrolinones bearing aza-quaternary stereocenters. To the best of our knowledge, this reaction represents the first example of organocatalyzed multicomponent asymmetric 1,2-rearrangements. The first organocatalyzed multicomponent asymmetric 1,2-rearrangement is established, which provides a straightforward access to 2,2-disubstituted pyrrolinones in excellent chemo- and stereoselectivities. This reaction also represents the first example of asymmetric catalytic construction of chiral pyrrolinones bearing aza-quaternary stereocenters.image The 1,2-rearrangement reaction is one of the most important approaches to construct carbon-carbon bonds in organic synthesis. However, the development of catalytic asymmetric 1,2-rearrangements is still far from mature and often suffers from problems such as complex substrates, single product structure, and lack of synthetic application. Multicomponent reaction has been recognized as a robust tool for the synthesis of diverse and tunable products from readily available starting material. Conceptionally and practically, the development of multicomponent asymmetric 1,2-rearrangements is highly desirable. In this regard, we report herein a three-component benzilic acid-type rearrangement of 2,3-diketoesters, aromatic amines and aldehydes for the asymmetric construction of synthetically challenging pyrrolinones bearing aza-quaternary stereocenters. To the best of our knowledge, this reaction represents the first example of organocatalyzed multicomponent asymmetric 1,2-rearrangements. The 1,2-rearrangement reaction is one of the most important approaches to construct carbon-carbon bonds in organic synthesis. However, the development of catalytic asymmetric 1,2-rearrangements is still far from mature and often suffers from problems such as complex substrates, single product structure, and lack of synthetic application. Multicomponent reaction has been recognized as a robust tool for the synthesis of diverse and tunable products from readily available starting material. Conceptionally and practically, the development of multicomponent asymmetric 1,2-rearrangements is highly desirable. In this regard, we report herein a three-component benzilic acid-type rearrangement of 2,3-diketoesters, aromatic amines and aldehydes for the asymmetric construction of synthetically challenging pyrrolinones bearing aza-quaternary stereocenters. To the best of our knowledge, this reaction represents the first example of organocatalyzed multicomponent asymmetric 1,2-rearrangements.The 1,2-rearrangement reaction is one of the most important approaches to construct carbon-carbon bonds in organic synthesis. However, the development of catalytic asymmetric 1,2-rearrangements is still far from mature and often suffers from problems such as complex substrates, single product structure, and lack of synthetic application. Multicomponent reaction has been recognized as a robust tool for the synthesis of diverse and tunable products from readily available starting material. Conceptionally and practically, the development of multicomponent asymmetric 1,2-rearrangements is highly desirable. In this regard, we report herein a three-component benzilic acid-type rearrangement of 2,3-diketoesters, aromatic amines and aldehydes for the asymmetric construction of synthetically challenging pyrrolinones bearing aza-quaternary stereocenters. To the best of our knowledge, this reaction represents the first example of organocatalyzed multicomponent asymmetric 1,2-rearrangements. The 1,2‐rearrangement reaction is one of the most important approaches to construct carbon‐carbon bonds in organic synthesis. However, the development of catalytic asymmetric 1,2‐rearrangements is still far from mature and often suffers from problems such as complex substrates, single product structure, and lack of synthetic application. Multicomponent reaction has been recognized as a robust tool for the synthesis of diverse and tunable products from readily available starting material. Conceptionally and practically, the development of multicomponent asymmetric 1,2‐rearrangements is highly desirable. In this regard, we report herein a three‐component benzilic acid‐type rearrangement of 2,3‐diketoesters, aromatic amines and aldehydes for the asymmetric construction of synthetically challenging pyrrolinones bearing aza‐quaternary stereocenters. To the best of our knowledge, this reaction represents the first example of organocatalyzed multicomponent asymmetric 1,2‐rearrangements. The first organocatalyzed multicomponent asymmetric 1,2‐rearrangement is established, which provides a straightforward access to 2,2‐disubstituted pyrrolinones in excellent chemo‐ and stereoselectivities. This reaction also represents the first example of asymmetric catalytic construction of chiral pyrrolinones bearing aza‐quaternary stereocenters.
Author	He, Yu‐Ping Wu, Hua Li, Xing‐Zi
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Keywords	MIGRATION ALDEHYDE Pyrrolinones Multicomponent Reaction VICINAL TRICARBONYLS Organocatalysis Quaternary Stereocenter 1,2-Rearrangement AMINES BENZILIC ACID REARRANGEMENTS CHEMISTRY SUBSTITUTED PYRROLIN-4-ONES EFFICIENT ACCESS quaternary stereocenter pyrrolinones multicomponent reaction 1,2-rearrangement
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Snippet	The 1,2‐rearrangement reaction is one of the most important approaches to construct carbon‐carbon bonds in organic synthesis. However, the development of... The 1,2-rearrangement reaction is one of the most important approaches to construct carbon-carbon bonds in organic synthesis. However, the development of...
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SubjectTerms	1,2-Rearrangement Aldehydes Amines Asymmetry Benzilic acid Carbon Chemical synthesis Chemistry Chemistry, Multidisciplinary Enantiomers Multicomponent Reaction Organocatalysis Physical Sciences Pyrrolinones Quaternary Stereocenter Science & Technology Substrates
Title	Multicomponent Cyclizative 1,2‐Rearrangement Enabled Enantioselective Construction of 2,2‐Disubstituted Pyrrolinones
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