A new synthesis of (+)- and (−)-cherylline

Lebrun, Stéphane; Couture, Axel; Deniau, Éric; Grandclaudon, Pierre

doi:10.1039/b302168h

Cited by 24 publications

(10 citation statements)

References 46 publications

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“…It has been noticed long ago that the major groove edges of WC base pairs have complementary hydrogen bonding (H-bonding) patterns [22,23]. An infinite helical quadruplex using major groove association between WC pairs was predicted by manual modeling [11] and discussed as an intermediate state in homologous recombination [12,24]. Experimentally, such structures were not found, but the possibility of major groove H-bonding was confirmed [25,26].…”

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confidence: 99%

Homologous Pairing between Long DNA Double Helices

Mazur

2016

Phys. Rev. Lett.

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Molecular recognition between two double stranded (ds) DNA with homologous sequences may not seem compatible with the B-DNA structure because the sequence information is hidden when it is used for joining the two strands. Nevertheless, it has to be invoked to account for various biological data. Using quantum chemistry, molecular mechanics, and hints from recent genetics experiments, I show here that direct recognition between homologous dsDNA is possible through the formation of short quadruplexes due to direct complementary hydrogen bonding of major-groove surfaces in parallel alignment. The constraints imposed by the predicted structures of the recognition units determine the mechanism of complexation between long dsDNA. This mechanism and concomitant predictions agree with the available experimental data and shed light upon the sequence effects and the possible involvement of topoisomerase II in the recognition.

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confidence: 99%

Homologous Pairing between Long DNA Double Helices

Mazur

2016

Phys. Rev. Lett.

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“…Differently substituted arylboronic acids 2 and enones 1a-c, g underwent this reaction under the optimized reaction conditions, and the results are shown in Table 60 (Scheme 95). 197 The use of ligand L54b can be also expanded to the Rh(I)-catalyzed stereoselective addition of differently substituted arylboronic acids to tert-butyl cinnamate 195 under similar conditions to afford the desired products 196a, b in satisfactory chemical yields and with good ee's which required no further optimization (Scheme 96). 197 The Rh/diene-catalyzed 1,4-additions of sodium tetraarylborates 167a-c, e-g to b,b-disubstituted a,b-unsaturated esters 197d-h afforded 198a-j in satisfactory yields.…”

Section: Table 48mentioning

confidence: 98%

“…197 The use of ligand L54b can be also expanded to the Rh(I)-catalyzed stereoselective addition of differently substituted arylboronic acids to tert-butyl cinnamate 195 under similar conditions to afford the desired products 196a, b in satisfactory chemical yields and with good ee's which required no further optimization (Scheme 96). 197 The Rh/diene-catalyzed 1,4-additions of sodium tetraarylborates 167a-c, e-g to b,b-disubstituted a,b-unsaturated esters 197d-h afforded 198a-j in satisfactory yields. An efficient and highly asymmetric catalysis has also been achieved to generate quaternary carbon stereogenic centers at the b-position of esters by tuning the ester group of the substrates and using chiral diene (R)-L55 as the ligand.…”

Section: Table 48mentioning

confidence: 98%

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

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

106

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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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“…α,α‐Diaryl acetamides are an important structural unit in medicinal chemistry . In particular, their reduced forms (chiral β,β‐diarylamines) exist in many therapeutic agents or alkaloids such as diclofensine, nomifensine, and cherylline (Figure ). Despite their biological relevance, an efficient preparation of chiral α,α‐diaryl acetamides is not available.…”

Section: Figurementioning

confidence: 99%

Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group

Tian

Guo-xian

et al. 2018

Angew Chem Int Ed

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Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral α-aryl-α-mesylated acetamides and arylboronic acids provided access to a series of chiral α,α-diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB receptor ligand, the antidepressant (S)-diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method.

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A new synthesis of (+)- and (−)-cherylline

Cited by 24 publications

References 46 publications

Homologous Pairing between Long DNA Double Helices

Homologous Pairing between Long DNA Double Helices

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

Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group

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