Highly enantioselective Friedel–Crafts alkylation reaction catalyzed by rosin-derived tertiary amine–thiourea: synthesis of modified chromanes with anticancer potency

Jiang, Xianxing; Wu, Lipeng; Xing, Yanhong; Wang, Long; Wang, Shoulei; Chen, Zongyao; Wang, Rui

doi:10.1039/c1cc14379d

Cited by 74 publications

(32 citation statements)

References 25 publications

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“…The α‐carbon atom of naphthols might be activated by an interaction between the adjoining tertiary amine scaffold of this catalyst and the hydroxy group in naphthols, together with β,γ‐unsaturated α‐ketoester derivatives were fixed and activated by the two thiourea hydrogen atoms through weak hydrogen bonds. Successively, the attack of the incoming nucleophiles to the Si ‐face of β,γ‐unsaturated α‐ketoester derivatives happen and then endures a hemiketal cyclization reaction to give corresponding product, that is consistent with the experimental consequences …”

Section: Organocatalyzed Asymmetric Friedel‐crafts Reactions Usingsupporting

confidence: 79%

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Organocatalyzed Asymmetric Friedel‐Crafts Reactions: An Update

Heravi

Zadsirjan

Heydari

et al. 2019

The Chemical Record

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The Friedel‐Crafts alkylation (F‐CA) reaction is a special kind of carbon−carbon bond formations, which is frequently being used for the formation of such bond in some aromatic rings in organic synthesis. Its asymmetric variant gives enantiorich products. Commonly, an in situ organocatalyzed asymmetric Friedel‐Crafts alkylation (AF‐CA) proceeds via generation of an enamine as an intermediate. The organocatalyzed‐AF‐CA was discovered and established in the mid‐1980s and reviewed comprehensively in 2010. In this report, we are trying to update the applications of novel organocatalysts in the AF‐CA as a versatile synthetic strategy, which is frequently used in the effective asymmetric synthesis of complex molecules, pharmaceutically important compounds and most importantly in the total synthesis of biologically active natural products.

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Section: Organocatalyzed Asymmetric Friedel‐crafts Reactions Usingsupporting

confidence: 79%

“…Furthermore, the transformations using 143 have been tested. Pleasantly, all reactions gave the opposite enantiomeric products with moderate yields and moderate to high ee s (Scheme , Table ) …”

Section: Organocatalyzed Asymmetric Friedel‐crafts Reactions Usingmentioning

confidence: 99%

Organocatalyzed Asymmetric Friedel‐Crafts Reactions: An Update

Heravi

Zadsirjan

Heydari

et al. 2019

The Chemical Record

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“…developed a Friedel–Crafts alkylation of 1‐ or 2‐naphthols and β,γ‐unsaturated α‐keto esters. A chiral rosin‐derived thiourea catalyst 271 is deployed and the corresponding chromones are accomplished in good yields and excellent ee values (Scheme ) 301…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

“…A chiral rosin-derived thiourea catalyst 271 is deployed and the corresponding chromones are accomplished in good yields and excellent ee values (Scheme 159). [301] Substrates bearing cumulated double bonds are highly reactive and consequently interesting starting compounds for organocatalytic transformations. In this context Fu et al demonstrated their convenience for g-additions of malo-nates to allenoates and Weinreb allenamides.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Scheffler

Mahrwald

2013

Chemistry A European J

200

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Beyond a doubt organocatalysis belongs to the most exciting and innovative chapters of organic chemistry today. Organocatalysis has emerged not only as a complement to metal-catalyzed reactions and to biocatalysis over the last decade, but also provides new asymmetric organocatalyzed reactions that cannot be accomplished by metal- or biocatalyzed reactions so far. A large number of organocatalytic processes are already well established in organic synthesis. Nevertheless, the number of publications in this field is still on the increase; new important results are produced constantly. This review gives a detailed overview of the latest developments and main streams in organocatalyzed asymmetric CC bond formation processes of the last three years. It is intended to outline the most important current findings focused on especially new synthetic methodologies.

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“…Rosin-derived bifunctional thiourea organocatalysts, originated from the abundantly available natural rosin, were revealed to be highly efficient for some catalytic asymmetric reactions, including Aza-Henry [28], Mannich reaction [29,30], Aldol reaction [31,32], Michael addition [33][34][35][36], and Friedel-Crafts alkylation [37]. The thiourea moiety of those organocatalysts is usually introduced at position C-4 of rosin skeleton, while the tertiary amine moiety is either 1,2-diaminocyclohexane 1 or cinchona alkaloid 2 (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Michael Addition of Malononitrile with Chalcones via Rosin-Derived Bifunctional Squaramide

et al. 2019

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A rosin-derived bifunctional squaramide catalyzed asymmetric Michael addition of malononitrile with chalcones was discovered. This protocol provides a methodology for the facile synthesis of chiral γ-cyano carbonyl compounds in high yields and enantioselectivities (up to 99% yield and 90% ee) with a lower catalyst loading (0.3 mol%). The predominant R-configured adducts were obtained by this organocatalystic reaction, according to the experimental findings.Catalysts 2020, 10, 14 2 of 11 malononitrile and chalcones. As our ongoing interest in organocatalysis of rosin-derived catalysts, we herein reported the results from the asymmetric Michael addition of malononitrile with chalcones catalyzed by rosin-derived bifunctional squaramide organocatalysts.

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Highly enantioselective Friedel–Crafts alkylation reaction catalyzed by rosin-derived tertiary amine–thiourea: synthesis of modified chromanes with anticancer potency

Abstract: We present herein for the first time the synthesis and preliminary biological evaluation of various modified chromanes via a rosin-derived tertiary amine-thiourea-catalyzed highly enantioselective Friedel-Crafts alkylation reaction.

Cited by 74 publications

References 25 publications

Organocatalyzed Asymmetric Friedel‐Crafts Reactions: An Update

Organocatalyzed Asymmetric Friedel‐Crafts Reactions: An Update

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Asymmetric Michael Addition of Malononitrile with Chalcones via Rosin-Derived Bifunctional Squaramide

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