Rhodium-Catalyzed 1,4-Addition of Arylboronic Acids to 3-Benzylidene-1H-pyrrolo[2,3-b]pyridin-2(3H)-one Derivatives

Croix, Cécile; Prié, Gildas; Chaulet, Charlotte; Viaud‐Massuard, Marie‐Claude

doi:10.1021/jo502784h

Cited by 9 publications

(5 citation statements)

References 46 publications

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“…Viaud-Massuard [190] developed the asymmetric addition on 7-azaindoles as an example of an exocyclic benzylidene lactamyl Michael acceptor. The reaction was performed in the presence of the ( R , R )-Phbod ligand, which ensured the 94% ee of the indole-based product (Table 11, entry 1).…”

Section: Chemical Transformations Of Indolylboronic Acid Derivativesmentioning

confidence: 99%

“…A ligandless condition was described by Howell et al (Table 11, entry 2) [191]. They studied the Michael addition of boronic acids onto α-methylene-β-lactones under similar reaction conditions [190]. Generally speaking, the reaction provided a mixture of diastereomers, including β-propiolactone substituted by a 1-methyl-5-indolyl substituent.…”

Section: Chemical Transformations Of Indolylboronic Acid Derivativesmentioning

confidence: 99%

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Indolylboronic Acids: Preparation and Applications

et al. 2019

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Indole derivatives are associated with a variety of both biological activities and applications in the field of material chemistry. A number of different strategies for synthesizing substituted indoles by means of the reactions of indolylboronic acids with electrophilic compounds are considered the methods of choice for modifying indoles because indolylboronic acids are easily available, stable, non-toxic and new reactions using indolylboronic acids have been described in the literature. Thus, the aim of this review is to summarize the methods available for the preparation of indolylboronic acids as well as their chemical transformations. The review covers the period 2010–2019.

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Section: Chemical Transformations Of Indolylboronic Acid Derivativesmentioning

confidence: 99%

Section: Chemical Transformations Of Indolylboronic Acid Derivativesmentioning

confidence: 99%

Indolylboronic Acids: Preparation and Applications

et al. 2019

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“…In most of the reported cases, ee values of less than 96% have been claimed (Scheme 158). [283][284][285][286][287][288][289] Apparently, there is no highly enantioselective (>98% ee) 290,291 general catalyst for the arylation of acyclic (E)-enones, dissimilar to their corresponding cyclic (Z)-isomers (Table 99) A novel and efficient type of achiral diene-Rh-catalyzed stereoselective arylation was developed and reported. 292 3-Sulfolene 300 is in equilibration with 2-sulfolene 301 via base-catalyzed isomerization under Rh-catalyzed arylation conditions.…”

Section: Table 48mentioning

confidence: 99%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

107

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Rh-catalyzed asymmetric 1,4-addition reactions to a,b-unsaturated carbonyl and related compounds: an update Available online xxxx Dedicated to my son, OMID on the occasion of his 35th birthday. a b s t r a c tThe Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to an appropriate receptor has been a growing area of research over the last decade. The receptors for such a 1,4-addition reaction are chiefly a,b-unsaturated ketones, esters, amides, enones, nitroalkenes, and occasionally phosphonates etc. This reaction in the presence of chiral rhodium complexes introduce the aryl and alkenyl groups at the b-position of the above electron poor olefins, enantioselectively. Chiral Rh complexes similar to other transition metals can be added to some electron poor olefins, in turn making them viable to attack by various organometallic reagents for highly enantioselective C-C bond formation. The Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to electron poor olefins has been reviewed in 2003. Due to the importance of the asymmetric C-C bond formation via 1,4-conjugate addition reactions and the number of such reactions catalyzed by Rh-complexes, in this review we highlight the recent advances in Rh-complex asymmetric catalyzed 1,4-addition reactions since 2003.

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“…A broad scope of substrates such as cyclic or acyclic enones and enoates have been reported [ 18 , 19 ]. Rhodium(I) complexes have been demonstrated to be excellent catalysts for 1,4-conjugate addition of alkenyl- and arylboronic acids to α,β-unsaturated ketones, esters, and even less reactive amides [ 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

“…Recent advances in the NHC-Cu-catalyzed conjugate arylation of β-substututed cyclic enones to afford quaternary stereogenic centers has also been reported [ 52 ]. Despite the fact that rhodium(I)-complexes-catalyzed 1,4-conjugate addition of boronic acids is one of the most potent methods for C-C bond formation, there are no reported examples on 1,4-conjugate addition of boronic acids to N -Boc-4-pyridones or substrates that contain piperidine subunits, presumably due to the unreactive nature of these nitrogen-containing substrates with boronic acids [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone

et al. 2017

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Rhodium(I)-complexes catalyzed the 1,4-conjugate addition of arylzinc chlorides to N-Boc-4-pyridone in the presence of chlorotrimethylsilane (TMSCl). A combination of [RhCl(C2H4)2]2 and BINAP was determined to be the most effective catalyst to promote the 1,4-conjugate addition reactions of arylzinc chlorides to N-Boc-4-pyridone. A broad scope of arylzinc reagents with both electron-withdrawing and electron-donating substituents on the aromatic ring successfully underwent 1,4-conjugate addition to N-Boc-4-pyridone to afford versatile 1,4-adducts 2-substituted-2,3-dihydropyridones in good to excellent yields (up to 91%) and excellent ee (up to 96%) when (S)-BINAP was used as chiral ligand.

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Rhodium-Catalyzed 1,4-Addition of Arylboronic Acids to 3-Benzylidene-1H-pyrrolo[2,3-b]pyridin-2(3H)-one Derivatives

Cited by 9 publications

References 46 publications

Indolylboronic Acids: Preparation and Applications

Indolylboronic Acids: Preparation and Applications

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone

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