Boron Trichloride/Tetra-<i>n</i>-Butylammonium Iodide:  A Mild, Selective Combination Reagent for the Cleavage of Primary Alkyl Aryl Ethers

Brooks, Paige R.; Wirtz, Michael; Vetelino, Michael G.; Rescek, Diane M.; Woodworth, Graeme F.; Morgan, and Bradley P.; Coe, Jotham W.

doi:10.1021/jo9910740

Cited by 112 publications

(63 citation statements)

References 34 publications

(24 reference statements)

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“…Protected resveratrol 6 could therefore be obtained by a simple filtration followed by flash-chromatographic purification. Demethylation of (E)-3,4Ј,5-trimethoxystilbene by treatment with boron tribromide [18] or with the recently described boron trichloride/tetra-n-butylammonium iodide reagent [19] cleanly afforded pure resveratrol in 80 % overall yield.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of (E)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis

et al. 2005

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An efficient and highly stereoselective synthetic procedure is reported for the construction of symmetrical and unsymmetrical (E)-polymethoxystilbene and (E)-polyhydroxystilbene derivatives. The strategy rests on a cross-metathesis reaction catalyzed by stable, well-defined (alkylidene)ruthenium complexes, in particular the second-generation Grubbs catalyst [RuCl 2 (=CHPh)(SIMes)(PCy 3 )] [SIMes = 1,3-

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Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of (E)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis

et al. 2005

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“…Treatment of 13 with BBr 3 in CH 2 Cl 2 [50] resulted in complete decomposition of the fullerene compound, as indicated by a strong color change. The use of LiI/SiCl 4 /BF 3 ·OEt 2 , [51] BCl 3 , [52] BCl 3 /NBu 4 + Br À [53] , or HBr/H 3 CCOOH as ethercleaving reagents showed no conversion of the reactant even after several days and at higher temperatures. In contrast, after heating a solution of 13 and NaI in HBr/ H 3 CCOOH (1:1) and CHCl 3 to reflux, cleavage of one ether bond could be detected by mass-spectrometric analysis, but this deprotection was reversible.…”

Section: Selective Functionalization Of the Equatorial Addend Zonementioning

confidence: 99%

Synthesis and Orthogonal Functionalization of [60]Fullerene e,e,e‐Trisadducts with Two Spherically Defined Addend Zones

Beuerle

Hirsch

2009

Chemistry A European J

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e,e,e-Trisadducts 13 and 15 have been prepared by a highly regioselective threefold cyclopropanation of tripodal malonates 10 and 12 with C60. The yield and regioselectivity depend on the length and structure of the tethers that connect the malonate units to the focal benzene core of 13-15. As a consequence of the template-directed synthesis, all e,e,e-trisadducts were formed as in/out isomers exclusively and contain two spherically well-defined addend zones with equatorial and polar orientation, respectively. By variation of the outer malonate termini of the tethers, selective functionalization of the equatorial addend zone could be achieved, thus leading to fine-tuning of intermolecular interactions, such as solubility or aggregation phenomena. After removal of the focal benzene moiety in 14 and 15, selective functionalization of the polar addend zone could be achieved. Strong intramolecular hydrogen-bonding networks of the polar substituents in the polar addend zone could be observed by 1H NMR spectroscopic analysis. By orthogonal functionalization of both addend zones, fullerene derivatives 44-48 could be synthesized as one single in/out isomer, thus greatly enhancing the potential of e,e,e-trisadducts as building blocks in supramolecular architectures.

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“…50) The use of an odorless sulfide instead of dimethyl sulfide made little difference (Table 3, Entries 3, 5). Deprotection of benzyl ethers with boron trichloride [55][56][57][58] could favorably afford in an excellent yield (95%) of 8b (Table 3, Entry 6).…”

Section: Resultsmentioning

confidence: 72%

“…[55][56][57][58] In the first strategy of transformation from 32 to (Ϫ)-1, we tried to remove the chiral imidazolidinone moiety in the early steps since the presence of a fused ring caused complexities and broadness of the NMR spectra, which interfered with structure analysis. Thus, 32 was first reduced with L-Selectride to afford allyl alcohol 33, where hydrolysis with sodium hydroxide to imine 34 via secondary amine 35 proceeded smoothly at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Biomimetic Synthesis of (.+-.)-Galanthamine and Asymmetric Synthesis of (-)-Galanthamine Using Remote Asymmetric Induction

Node

Kodama

Hamashima

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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(؎)-Galanthamine (1) was synthesized in excellent yield by applying PIFA-mediated oxidative phenol coupling of N-(4-hydroxy)phenethyl-N-(3,4,5-trialkoxy)benzyl formamide (15b) as a key step. Because of the symmetrical characteristics of the pyrogallol moiety in the substrate (15b), the phenol coupling resulted in a sole coupling product except for volatile components from the oxidizing agent. On the basis of the successful results of the above strategy, (؊)-galanthamine (1) was synthesized by employing a novel remote asymmetric induction, where conformation of the seven-membered ring in the product of the phenol coupling was restricted by forming a fused-chiral imidazolidinone ring with D-phenylalanine on the benzylic C-N bond of the tri-O-alkylated gallyl amino moiety. The conformational restriction and successive debenzylation of the protected hydroxyl groups on the pyrogallol ring caused diastereoselective cyclization to yield a cyclic ether having the desired stereochemistry for the synthesis of (؊)-1.

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Boron Trichloride/Tetra-n-Butylammonium Iodide: A Mild, Selective Combination Reagent for the Cleavage of Primary Alkyl Aryl Ethers

Cited by 112 publications

References 34 publications

Stereoselective Synthesis of (E)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis

Stereoselective Synthesis of (E)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis

Synthesis and Orthogonal Functionalization of [60]Fullerene e,e,e‐Trisadducts with Two Spherically Defined Addend Zones

Biomimetic Synthesis of (.+-.)-Galanthamine and Asymmetric Synthesis of (-)-Galanthamine Using Remote Asymmetric Induction

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