Selective Access to Both Diastereoisomers in an Enantioselective Intramolecular Michael Reaction by Using a Single Chiral Organocatalyst and Application in the Formal Total Synthesis of (−)‐Epibatidine

Jensen, Kristoffer; Weise, Christian F.; Dickmeiss, Gustav; Morana, Fabio; Davis, Rebecca L.; Jørgensen, Karl Anker

doi:10.1002/chem.201202353

Cited by 27 publications

(3 citation statements)

References 46 publications

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“…Jørgensen synthesized both cis ‐ and trans ‐4‐nitro‐3‐substituted cyclohexanones by adjusting the reaction conditions in the intramolecular Michael reaction of ( E )‐6‐nitro‐1‐substituted hex‐1‐en‐3‐ones, which was catalyzed by the ( S )‐ N ‐Boc‐phenylglycine salt of cinchona‐alkaloid‐derived primary aminocatalyst 117 (Scheme ) …”

Section: Reaction Condition‐dependent Diastereodivergencymentioning

confidence: 99%

Catalytic Strategies for Diastereodivergent Synthesis

Lin

Feng

2017

Chemistry A European J

216

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Chiral molecules with multiple stereocenters are widely distributed in nature and drugs. Asymmeric catalysis has allowed the formation of a chiral molecule's enantiomers with equal ease by applying the enantiomeric pair of a chiral catalyst. However, the diastereodivergent synthesis is a great challenge because the formation of one of the diastereomers is inherently preferred in most reactions. Under the efforts of chemists, elegant strategies have been developed to full control of absolute and relative stereochemical configurations. In this Minireview, we highlight the significant advances achieved in this field, and present the diastereo-control mechanism in the appropriate place on the expectation that new diastereodivergent strategies can be inspired and more types of enantioselective diastereodivergent reactions can be realized.

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Section: Reaction Condition‐dependent Diastereodivergencymentioning

confidence: 99%

Catalytic Strategies for Diastereodivergent Synthesis

Lin

Feng

2017

Chemistry A European J

216

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“…[4][5][6][7][8][9][10][11][12][13][14][15][16] Among the organocatalytic reactions, few have made their way into the total synthesis of natural products and drugs. [17][18][19] Organocatalytic Michael, [20][21][22] aldol, [23,24] Diels-Alder, [25] aminoxylation, [26] and Friedel-Crafts, [27] reactions are used as key steps in the total synthesis of natural products, drugs and drug intermediates.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic One‐Pot Synthesis of Pseudo‐Terpenoids

et al. 2022

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Structurally complex cedrane scaffolds were synthesized in very good yields with high chemo-and diastereoselectivities in a sequential one-pot manner. A combination of intermolecular olefination, intramolecular Michael and Michael reactions or intermolecular olefination, intramolecular Michael and aldol reactions were used as the key steps from the readily available hydroxy-p-quinone butanals and phosphoranes with catalytic amounts of quinine at ambient temperatures for a few hours. This is a unique one-pot combination of coupling and annulation routes for the green synthesis of a library of tricyclic pseudo-terpenoids (cedrane scaffolds) with high selectivity and yields. Organocatalytic ring isomerization was highlighted through transforming one ring into another one by retrocyclization. We have discussed thoroughly mechanistic aspects of these tandem coupling/annulation and ring isomerization reactions based on control experiments and X-ray crystal structure analysis.

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“…Even though there exist a considerable number of organo-catalytic asymmetric methods, only a few among them have made their way into the total synthesis of natural products and their analogs [ 17 , 18 , 19 ]. Among the known organocatalytic reactions, Michael [ 20 , 21 , 22 ], aldol [ 23 , 24 ], Diels–Alder [ 25 ] and Friedel–Crafts [ 26 ] reactions are the ones which have been repeatedly used in asymmetric total synthesis of natural products, drugs and drug intermediates.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Enantiospecific Total Synthesis of Butenolides

2021

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Biologically important, chiral natural products of butenolides, (−)-blastmycinolactol, (+)-blastmycinone, (−)-NFX-2, (+)-antimycinone, lipid metabolites, (+)-ancepsenolide, (+)-homoancepsenolide, mosquito larvicidal butenolide and their analogues were synthesized in very good yields in a sequential one-pot manner by using an organocatalytic reductive coupling and palladium-mediated reductive deoxygenation or organocatalytic reductive coupling and silica-mediated reductive deamination as the key steps.

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Selective Access to Both Diastereoisomers in an Enantioselective Intramolecular Michael Reaction by Using a Single Chiral Organocatalyst and Application in the Formal Total Synthesis of (−)‐Epibatidine

Cited by 27 publications

References 46 publications

Catalytic Strategies for Diastereodivergent Synthesis

Catalytic Strategies for Diastereodivergent Synthesis

Organocatalytic One‐Pot Synthesis of Pseudo‐Terpenoids

Organocatalytic Enantiospecific Total Synthesis of Butenolides

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