A Simple Synthetic Approach to 3,3‘-Diaryl BINOLs

Simonsen, Klaus B.; Gothelf, Kurt V.; Jørgensen, Karl Anker

doi:10.1021/jo980959t

Cited by 104 publications

(87 citation statements)

References 16 publications

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“…Ligand syntheses: The BINOL derivatives (R)-4 [13] and (R)-6 [14] were already available by literature procedures, while the BINOL derivatives (R)-5 and (R)-7 were prepared according to a synthetic strategy similar to the one developed by Pu et al [14] The central step in these syntheses is the formation of the bond between the BINOL and the phenyl substituent in a Suzuki coupling reaction. The relevant boronic acids were prepared by site-directed lithiation followed by reaction with the appropriate boron electrophile.…”

Section: Resultsmentioning

confidence: 99%

“…The ligands (R)-4 [13] and (R)-6 [14] were prepared as described in the literature. Benzaldehyde was distilled, kept, and handled under N 2 , and stored over 4 molecular sieves at 5 8C.…”

Section: Methodsmentioning

confidence: 99%

“…General methods: The 1 H and 13 C NMR spectra were recorded in CDCl 3 at 300 MHz and 75 MHz, respectively, using tetramethylsilane (TMS) or residual solvent as the reference and the deuterated solvent as lock. Chemical shifts are reported in ppm downfield from TMS.…”

Section: Methodsmentioning

confidence: 99%

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Development of an Unusually Highly Enantioselective Hetero-Diels-Alder Reaction of Benzaldehyde with Activated Dienes Catalyzed by Hypercoordinating Chiral Aluminum Complexes

et al. 2000

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The effect of Lewis acid catalysis of the hetero-Diels-Alder reaction between benzaldehyde and activated dienes (e.g. the Danishefsky's diene) has been investigated. In the present work we decided to study a series of chiral aluminum complexes as potential catalysts for the hetero-Diels-Alder reaction in order to gain a better understanding of the effect on the chiral induction of varying the steric and electronic environment of the metal ion. The results of this study prompted us to conclude that steric effects in the ligand coordination sphere and hypercoordination are strongly contributing factors to the optical yield of the reaction. Optimization of the reaction culminated in the synthesis of the hetero-Diels-Alder product in 99.4% ee and 97% yield of the isolated product. Based on the experimental results the mechanism for the hetero-Diels-Alder reaction is discussed and it is postulated that hypercoordination to the chiral aluminum Lewis acid center is of importance for the reaction.

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Section: Resultsmentioning

confidence: 99%

“…The ligands (R)-4 [13] and (R)-6 [14] were prepared as described in the literature. Benzaldehyde was distilled, kept, and handled under N 2 , and stored over 4 molecular sieves at 5 8C.…”

Section: Methodsmentioning

confidence: 99%

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Development of an Unusually Highly Enantioselective Hetero-Diels-Alder Reaction of Benzaldehyde with Activated Dienes Catalyzed by Hypercoordinating Chiral Aluminum Complexes

et al. 2000

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“…[12] The active catalyst was formed in situ by mixing the ligand with titanium tetraisopropoxide in toluene. [13] In this reaction, the molar ratio of ligand:Ti(O i Pr) 4 : Et 2 Zn:benzaldehyde was set up to be 0.1 : 1.2 : 3:1. (S)-1, (S)-2 and (S)-3 showed moderate catalytic properties and (S)-3 gave the best result (entry 3, 77.5% ee).…”

Section: Asymmetric Addition Of Diethylzinc To Aldehydesmentioning

confidence: 99%

“…Simonsen et al reported the synthesis of 3,3 -diaryl-BINOLs by reaction of 2,2 -dimethoxy-1,1 -binaphthyl-3,3 -diyldiboronic acid with aryl bromides using the Suzuki cross-coupling reaction. [4] Jin et al synthesized 3,3 -dipyridyl BINOLs by Suzuki coupling. [5] Recently, Matsui et al reported the synthesis of BINOLs 3-substituted by various pyridyls or pyridinylaminomethyls.…”

Section: Introductionmentioning

confidence: 99%

A facile synthesis and asymmetric catalytic activity of new 3‐substituted chiral BINOL ligands

Liu

Cao

Dong

et al. 2008

Applied Organom Chemis

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The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A)

et al. 2000

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Eine intramolekulare Diels‐Alder‐Reaktion mit substratvermittelter Kontrolle der Diastereoselektivität war die Grundlage für die asymmetrische Synthese des Grundgerüsts der CP‐Verbindungen 2. Das gezielt entworfene Trien 1 – es enthält eine sperrige chirale Gruppe, die die Seitenselektivität der Cycloaddition beeinflusst – wurde mit 70 % de zum Hauptdiastereomer 2 umgesetzt (siehe Schema). Die Aufklärung der absoluten Konfiguration dieser Vorstufe ermöglichte die enantioselektive Synthese der bioaktiven CP‐Moleküle und eröffnet nun den Zugang zu einfacheren, optisch aktiven Analoga.

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A Simple Synthetic Approach to 3,3‘-Diaryl BINOLs

Cited by 104 publications

References 16 publications

Development of an Unusually Highly Enantioselective Hetero-Diels-Alder Reaction of Benzaldehyde with Activated Dienes Catalyzed by Hypercoordinating Chiral Aluminum Complexes

Development of an Unusually Highly Enantioselective Hetero-Diels-Alder Reaction of Benzaldehyde with Activated Dienes Catalyzed by Hypercoordinating Chiral Aluminum Complexes

A facile synthesis and asymmetric catalytic activity of new 3‐substituted chiral BINOL ligands

The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A)

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