Asymmetric Construction of Stereogenic Carbon Centers Featuring a Trifluoromethyl Group from Prochiral Trifluoromethylated Substrates

Nie, Jing; Guo, Hongchao; Cahard, Dominique; Ma, Jun‐An

doi:10.1021/cr100166a

Cited by 994 publications

(234 citation statements)

References 430 publications

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“…有机氟化合物的化学也是一个发展迅速的领域, 由于它在新药研发和材料科学等很多领域里面都有应用 [24,25] , 特别是手性三氟甲基取代的含氟化合物的作用尤为突出 [26] . 2011 年, 王春江课题组 [27 [30] .…”

Section: S-michael 加成反应unclassified

Rencent Advances in Asymmetric Michael Addition Catalyzed by Chiral Bifunctional Thioureas

Hou¹,

Ma²,

Wang³

et al. 2014

Chin. J. Org. Chem.

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Asymmetric organocatalysis has been a frontier in the field of asymmetric catalysis. The comparable advantages, including mild reaction conditions, environment benign, and so on, render the organocatalytic reaction to possess some features of green chemistry. Chiral amino-thiourea organocatalyst, especially chiral bifunctional thiourea, has been shown excellent catalytic performance in a variety of asymmetric reactions. This review provides an overview of applications of chiral bifunctional thiourea in asymmetry Michael addition reaction, and the prospect and development are depicted finally.

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Section: S-michael 加成反应unclassified

Rencent Advances in Asymmetric Michael Addition Catalyzed by Chiral Bifunctional Thioureas

Hou¹,

Ma²,

Wang³

et al. 2014

Chin. J. Org. Chem.

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“…[7][8][9][10][11] As an alternative approach to producing CF 3-containing value-added functional molecules, transformations of readily available CF 3 -containing substrates are simple and practical. 12) The aldol reaction, among other approaches, exploiting trifluoromethyl ketones as electrophiles is an attractive transformation that provides biologically relevant α-CF 3 tertiary alcohols. [13][14][15] In this context, organocatalysts are highly effective catalysts for the introduction of ketones to trifluoromethyl ketones in asymmetric aldol reactions.…”

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confidence: 99%

Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones

et al. 2018

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SummaryA catalytic carboxylic acid-selective aldol reaction with trifluoromethyl ketones was developed. Reversible and selective covalent bond formation between a boron catalyst and a carboxylic acid is key to realizing the unprecedented catalytic aldol reaction of simple carboxylic acids. The reaction proceeded chemoselectively at the α-position of carboxylic acid even in the presence of ketone, ester, or amide functional groups in the donor substrates. The chemoselectivity is beneficial for late-stage derivatizations of biologically relevant compounds, as demonstrated by the conversion of indomethacin and triacetylcholic acid.

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“…2,3) Thus, the development of synthetic methods for 1-tetrasubstituted-2,2,2-trifluoroethylamines that cannot be accessed by hydrogenation of imines and reductive amination of ketones is an important challenge. 4,5) Catalytic nucleophilic addition to trifluoromethyl ketimines to gain access to these structures has been extensively studied over the last decade (Chart 1, Eq. a).…”

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confidence: 99%

“…a). 4,5) On the other hand, the reaction of 2,2,2-trifluoroethylamine derivatives with electrophiles is a complementary approach for the synthesis of 1-substituted-2,2,2-trifluoroethylamines (Chart 1, Eq. b).…”

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confidence: 99%

Synthesis of 1-Tetrasubstituted 2,2,2-Trifluoroethylamine Derivatives via Palladium-Catalyzed Allylation of sp3 C–H Bonds

Morisaki

Kondo

Sawa

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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This note describes the construction of tetrasubstituted carbon stereocenters via palladium-catalyzed allylation of sp 3 C-H bonds of 2,2,2-trifluoroethylamine derivatives. The presence of 2-pyridyl group of the imines derived from 1-substituted-2,2,2-trifluoroethylamine was key to promoting the reaction efficiently, allowing an access to a variety of 1-allylated 2,2,2-trifluoroethylamine derivatives with tetrasubstituted carbon stereocenters.

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Asymmetric Construction of Stereogenic Carbon Centers Featuring a Trifluoromethyl Group from Prochiral Trifluoromethylated Substrates

Cited by 994 publications

References 430 publications

Rencent Advances in Asymmetric Michael Addition Catalyzed by Chiral Bifunctional Thioureas

Rencent Advances in Asymmetric Michael Addition Catalyzed by Chiral Bifunctional Thioureas

Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones

Synthesis of 1-Tetrasubstituted 2,2,2-Trifluoroethylamine Derivatives <i>via</i> Palladium-Catalyzed Allylation of <i>sp</i><sup>3</sup> C–H Bonds

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