Organocatalytic Aza‐Michael–Michael Cascade Reactions: A Flexible Approach to 2,3,4‐Trisubstituted Tetrahydroquinolines

Jia, Zhen‐Xin; Luo, Yong‐Chun; Wang, Yao; Chen, Liang; Xu, Peng‐Fei; Wang, Binghe

doi:10.1002/chem.201201362

Cited by 71 publications

(22 citation statements)

References 59 publications

(2 reference statements)

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“…We found that the catalytic model proposed by Xu’s group could not explain our observed stereochemical result 5b. The configurations of products deduced following Xu’s model are opposite to those determined by X‐ray analysis.…”

Section: Resultscontrasting

confidence: 75%

Organocatalytic Enantioselective Cascade Aza‐Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines

Yang

Gao

et al. 2013

Adv Synth Catal

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An efficient organocatalytic highly asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of tetrahydroquinolines and tetrahydrochromanoquinolines has been developed. This cascade reaction proceeds well at low catalyst loading with a broad substrate scope, furnishing the desired products in excellent yields with excellent diastereoselectivities and enantioselectivities (up to > 99:1 dr, 99% ee) under mild conditions. Important-ly, it is the first catalytic asymmetric method for tetrahydrochromanoquinolines. This protocol provides a straightforward entry to highly functionalized chiral tetrahydroquinoline and tetrahydrochromanoquinoline derivatives from simple starting materials.

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Section: Resultscontrasting

confidence: 75%

Organocatalytic Enantioselective Cascade Aza‐Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines

Yang

Gao

et al. 2013

Adv Synth Catal

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“…Tetrahydroquinoline derivatives 445 were synthesized by Xu and co‐workers in 2012 via an asymmetric domino aza‐Michael/Michael reaction between ortho ‐aminophenyl‐substituted α,β‐unsaturated ketones 64 and nitroalkenes 446 , catalyzed by a quinidine‐derived thiourea 447 (Scheme ) . Du and co‐workers later obtained the same enantiomers of 445 in high stereoselectivities using a quinine‐derived squaramide 448 as the catalyst (Scheme ) .…”

Section: Multifunctional Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore,m imicking the biological process in the laboratory nowadays has the highest priority.T owards achieving this goal, designingorganic reactions in domino mode rathert han the multistep synthetic pathways andu sing organocatalysisi nstead of metal catalysis have received al ot of attention due to the inherenta dvantageso ft hese processes in terms of synthetic efficiencya nd sustainability.A saresult, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years.T his review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts andr eactionm odes.D iscussions on the reactionm echanismsa nd the applications of the developed domino reactionm ethodsi nt he synthesis of biologically active molecules and natural products are also includedwhen appropriate.

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“…The tricyclic backbone of compounds 5 is incorporated into Neurukin NK2 receptor antagonists, BKCa channel agonists, and liver x receptor (LXR) modulators . Compound 5b was prepared earlier as a mixture of diastereomers ( dr 87:13) from diastereomerically diverse tetrahydroquinoline 4b derived from unprotected ortho ‐aminochalcone 1′ . Using N ‐nosylated tetrahydroquinolines 3m – o , diastereomerically pure and readily attainable via the IVb ‐catalyzed asymmetric cascade reaction of 1b with 2a , 2d and 2i , respectively, we fulfilled a convenient stereospecific synthesis of compounds 4a – c and 5a – c as single diastereomers.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine

et al. 2018

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The most recyclable ionic liquid‐supported bifunctional tertiary amine–squaramide organocatalyst for the asymmetric domino reaction has been found. Over this catalyst, ortho‐aminochalcones protected with Tosyl or Nosyl groups underwent the aza‐Michael/Michael domino reaction with nitroolefins to afford corresponding 2,3,4‐trisubstituted tetrahydroquinolines as single diastereomers in nearly quantitative yield with up to 99 % ee. The catalyst was readily separated from the reaction mixture via a simple centrifugation/decantation workup and 19 times reused in the catalytic reaction without noticeable conversion or enantioselectivity reduction. The N‐nosylated products proved their synthetic value for pharmacology given their facile conversion to fused pirrolidino‐tetrahydroquinolines of high diastreomeric and enantiomeric purity via successive deprotection and reductive amination.

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Organocatalytic Aza‐Michael–Michael Cascade Reactions: A Flexible Approach to 2,3,4‐Trisubstituted Tetrahydroquinolines

Cited by 71 publications

References 59 publications

Organocatalytic Enantioselective Cascade Aza‐Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines

Organocatalytic Enantioselective Cascade Aza‐Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine

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