Rhodium-catalyzed convenient synthesis of functionalized tetrahydronaphthalenes

Tanaka, Ken; Sawada, Yayoi; Aida, Yusuke; Thammathevo, Maliny; Tanaka, Rie; Sagae, Hiromi; Otake, Yousuke

doi:10.1016/j.tet.2009.12.042

Cited by 17 publications

(10 citation statements)

References 54 publications

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“…Although neither theoretical studies addressing these issues nor any detailed studies regarding a ligand effect on the regioselectivity of cyclotrimerization between an unsymmetrically substituted diyne with a terminal alkyne have been published, several reports regarding ligand effect on the course of cyclotrimerization have been described. These involve: a) an effect of a ligand on regioselectvity of homocyclotrimerization catalyzed by Co‐,28a,b Rh‐28c and Ir‐complexes,28d b) on the course of Ir‐catalyzed cyclotrimerization of diynes with akynes,28e,f,g c) on regioselectivity of Rh‐catalyzed reaction of diyne with a disubstituted alkyne,28h d) on the rate of a Ni‐phosphine complex catalyzed homocyclotrimerization of 1,4‐butyndiol,28i,j and e) a Rh‐catalyzed cyclotrimerization of a symmetrical diyne with a disubstituted alkyne 28k. A distantly related study deals with the effect of variously substituted Cp′‐Rh complexes on co‐cyclotrimerization of terminal alkynes with nitriles 29.…”

Section: Resultsmentioning

confidence: 99%

[2+2+2]‐Cyclotrimerization of 1‐Cyclopropyl‐1,6‐diynes with Alkynes: Formation of Cyclopropylarenes.

et al. 2016

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Cyclotrimerization of 1-cyclopropyl-1,6diynes with various terminal alkynes wast ested under catalytic conditions using rhodium and ruthenium catalysts.W eo bserved that the regioselectivity of the reaction, that is,f ormation of 1,2-or 1,3-regioisomers,w as opposite for the two metals.F or the ruthenium complex[ Cp*Ru(cod)Cl]-catalyzed reactions the yieldsw ere in many cases high with as trong preference for the formation of 1,3-substituted regioisomers.I nt he case of catalysisb yt he rhodiumc omplex[ RhCl(PPh 3 ) 3 ], 1,2-substituted productsw ere generally preferred, albeit the selectivity waso ften modest.H owever, by changing the ligand environment around the central rhodium atom the regioselectivity as well as yields of the productsw eres ignificantly improved. Fore xample, by using ac ombination of the rhodium complex [Rh(cod) 2 BF 4 ]and 1,4-bis(diphenylphosphino)butane the regioselectivity wasc hanged from 1:1t o1 :12 in favor of the 1,2-regioisomer. This catalytic system was also applied for synthesis of as ubstituted 4-cyclopropyl-3-hydroisobenzofuran-1-one that could serve as ap otential intermediate for preparation of antihypertensivea gents.

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Section: Resultsmentioning

confidence: 99%

[2+2+2]‐Cyclotrimerization of 1‐Cyclopropyl‐1,6‐diynes with Alkynes: Formation of Cyclopropylarenes.

et al. 2016

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“…Tanaka et al described a regio- and enantioselective intermolecular 1,6-diyne-alkyne cycloaddition for the synthesis of optically active phthalides 579 . Thus, the Rh(I)-catalyzed reaction involving 1,6-diynes with an alkoxycarbonyl group at the alkyne terminus 577 and tertiary propargylic alcohols 578 gave phthalides 579 in the presence of chiral phosphine ligand 580 (Scheme ).…”

Section: Phthalidesmentioning

confidence: 99%

Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis

2014

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Scheme 10. Schmalz Synthesis of 3-Substituted Phthalides from 2-Formylketones Scheme 11. Enantioselective Synthesis of Phthalides via Ketone Hydroacylation Scheme 12. Synthesis of 3-Alkylphthalides from Sulfonylmethyl Benzoic Acids Scheme 13. Synthesis of an Isobenzofuranone via Thermolysis of a Bromomethylbenzoate Scheme 14. Kraus Approach to 3-Cyanophthalide Scheme 15. Ohzeki and Mori Synthesis of (−)-3-Butyl-7hydroxyphthalide Scheme 16. Asymmetric Dihydroxylation-Lactonization Route to Phthalides Chemical Reviews Review dx.

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“…It has been well-established that cyclotrimerization of monosubstituted diynes with terminal alkynes catalyzed by various Rh-catalysts favor the preferential formation of 1,2-isomers (ortho-isomers) [23] at the expense of 1,3-isomers (meta-isomers). However, the selectivity, i.e., 1,2-and 1,3-isomer ratios, can be controlled by the ligand environment around the central rhodium atom-at least to a certain level-as shown recently by us and others [24][25][26][27][28][29][30][31][32][33][34]. This is the result of the reaction mechanism, although the true nature of such regioselectivity has not yet been exactly comprehended.…”

Section: Synthesis Of 124-and 134-trisubstituted Fluorenolsmentioning

confidence: 95%

Synthesis of Tri- and Disubstituted Fluorenols and Derivatives Thereof Using Catalytic [2+2+2] Cyclotrimerization

et al. 2019

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A method for regioselective synthesis of 2,4-disubstituted and more highly substituted fluorenols using catalytic [2+2+2]cyclotrimerization of mono- and disubstituted diynes with terminal alkynes was explored. In the former case, the preferential formation of the 2,4-regioisomers was achieved in the presence of Cp*Ru(cod)Cl, whereas Rh-based catalysts tended to provide 3,4-regioisomers as the major products. The 2,4-disubstituted fluorenols were converted into the corresponding 9,9′-spirobifluorene derivatives and their structural and photophysical properties were evaluated.

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Rhodium-catalyzed convenient synthesis of functionalized tetrahydronaphthalenes

Cited by 17 publications

References 54 publications

[2+2+2]‐Cyclotrimerization of 1‐Cyclopropyl‐1,6‐diynes with Alkynes: Formation of Cyclopropylarenes.

[2+2+2]‐Cyclotrimerization of 1‐Cyclopropyl‐1,6‐diynes with Alkynes: Formation of Cyclopropylarenes.

Phthalides and Phthalans: Synthetic Methodologies and Their Applications in the Total Synthesis

Synthesis of Tri- and Disubstituted Fluorenols and Derivatives Thereof Using Catalytic [2+2+2] Cyclotrimerization

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