Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel–Crafts alkylation reaction

Wang, Shouguo; Long, Han; Zeng, Mi; Sun, Feng‐Lai; Zhang, Wei; You, Shu‐Li

doi:10.1039/c2ob07168a

Cited by 42 publications

(20 citation statements)

References 71 publications

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“…Carrying on the research, they later encountered a surprise when the same reaction catalyzed by N-triflylphosphoramide catalyst 48 gave the opposite absolute configuration, in generally very good yields and enantioselectivities (Scheme 57). 89 In both cases some substrate limitation was observed: the reaction performed best when the indole carried a methyl group at 2-position. Both free 2-position and a large 2-substituent led to poor yields and/or selectivities.…”

Section: -Indolyl(aryl)methanolsmentioning

confidence: 97%

Imine and iminium precursors as versatile intermediates in enantioselective organocatalysis

Kataja

Masson

2014

Tetrahedron

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Section: -Indolyl(aryl)methanolsmentioning

confidence: 97%

Imine and iminium precursors as versatile intermediates in enantioselective organocatalysis

Kataja

Masson

2014

Tetrahedron

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“…Commonly, all the tested 2‐methyl indole derivatives having both electron‐withdrawing and donating groups reacted easily to afford their desired cyclization products 15 with good ee s. Although, once indole has been used, both yield and enantioselectivity of the product have been remarkably reduced. The reaction with 2‐phenyl indole advanced easily in only 8 % yield and 28 % enantioselectivity (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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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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“…They obtained the aldol products in high yields with moderate to good enantioselectivities [101]. The chiral phosphoramidates used in this study and tested in many other enantioselective reactions (aldol reaction [102], Michael addition [103], Diels–Alder reaction [104], Friedel–Crafts alkylation [105]) illustrate the use of phosphoramidates as organocatalysts. These phosphoramidates were not synthesized by an AT reaction.…”

Section: Reviewmentioning

confidence: 99%

Atherton–Todd reaction: mechanism, scope and applications

Corre¹,

Berchel²,

Couthon‐Gourvès³

et al. 2014

Beilstein J. Org. Chem.

145

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SummaryInitially, the Atherton–Todd (AT) reaction was applied for the synthesis of phosphoramidates by reacting dialkyl phosphite with a primary amine in the presence of carbon tetrachloride. These reaction conditions were subsequently modified with the aim to optimize them and the reaction was extended to different nucleophiles. The mechanism of this reaction led to controversial reports over the past years and is adequately discussed. We also present the scope of the AT reaction. Finally, we investigate the AT reaction by means of exemplary applications, which mainly concern three topics. First, we discuss the activation of a phenol group as a phosphate which allows for subsequent transformations such as cross coupling and reduction. Next, we examine the AT reaction applied to produce fire retardant compounds. In the last section, we investigate the use of the AT reaction for the production of compounds employed for biological applications. The selected examples to illustrate the applications of the Atherton–Todd reaction mainly cover the past 15 years.

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Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel–Crafts alkylation reaction

Cited by 42 publications

References 71 publications

Imine and iminium precursors as versatile intermediates in enantioselective organocatalysis

Imine and iminium precursors as versatile intermediates in enantioselective organocatalysis

Organocatalyzed Asymmetric Friedel‐Crafts Reactions: An Update

Atherton–Todd reaction: mechanism, scope and applications

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