Processing of cyclopropylarenes by toluene dioxygenase: isolation and absolute configuration of metabolites

Finn, Kevin J.; Rochon, Lena; Hudlický, Tomáš

doi:10.1016/j.tetasy.2005.09.020

Cited by 10 publications

(4 citation statements)

References 12 publications

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“…3 The cyclopropylarene moiety can be found in a number of compounds possessing various biological activities, such as enzyme inhibitory,4 lipooxygenase inhibitory,5 anti‐HIV,6 antihepatitis,7 antiautoimmune,8 antihypertensive (Figure 1)9 or pesticidal effects 10. The cyclopropylarenes have also served as starting materials for synthesis of chiral intermediates via enzymatic oxidation 11. They are commonly prepared by cycloaddition of alkynes with dienes12 or cross‐coupling reactions using Suzuki13 or other protocols 14…”

Section: Introductionmentioning

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: Introductionmentioning

confidence: 99%

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

et al. 2016

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“…One more similar example includes the preparation of boronic acid (entry 4). 26 Later Deng and Wang performed cyclopropanation of Ealkenylboronic acid 3 to give a stereodefined trans-2-butylcyclopropylboronic acid (4) using the Simmons-Smith reaction; the reaction involved the use of the Zn-Cu couple and was promoted by a catalytic amount of chlorotrimethylsilane (Scheme 1). 27 Scheme 1 Zn-Cu-catalyzed chlorotrimethylsilane-mediated cyclopropanation of alkenylboronic acid 3…”

Section: With Methylene Synthetic Equivalentsmentioning

confidence: 99%

Cycloadditions of Alkenylboronic Derivatives

et al. 2020

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook

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“…42 To determine the absolute configuration of products obtained by whole-cell fermentation using toluene dioxygenase, Hudlicky and coworkers prepared cyclopropane 26 as a single diastereomer in 67% yield using the Et 2 Zn/CH 2 I 2 /CF 3 CO 2 H system (Scheme 9). 43 Mihovilovic and coworkers synthesized cyclopropane 28 as a substrate for a microbial Baeyer-Villiger oxidation study. After screening Simmons-Smith conditions using Cu/Zn couple and activated Zn, the Et 2 Zn/CH 2 I 2 /CF 3 CO 2 H system gave the best results for the cyclopropanation (Scheme 10).…”

Section: Applications Of the Roznch 2 Y Cyclopropanation Reagentmentioning

confidence: 99%

A novel class of tunable cyclopropanation reagents (RXZnCH2Y) and their synthetic applications

Cornwall

Wong

et al. 2012

Org. Biomol. Chem.

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The Simmons-Smith cyclopropanation is a widely used method to synthesize cyclopropanes from alkenes using methylene iodide and a zinc reagent. A novel class of organozinc species, RXZnCH 2 Y, has been found to efficiently cyclopropanate alkenes, including traditionally unreactive unfunctionalized alkenes. The reactivity and selectivity of this class of organozinc reagents can be regulated by tuning the electronic and/or steric nature of the RX group attached to Zn. During recent years, this class of organozinc reagent has been widely used in organic synthesis as a reagent for cyclopropanation and other useful synthetic transformations. Catalytic, asymmetric versions of this reaction have been developed providing high enantiomeric excess for unfunctionalized olefins. On Lo AndreaWong was born in Hong Kong in 1981. She moved to Honolulu, Hawai'i in 1994 and received her B.Sc. degree in chemistry from the University of Hawai'i at Mānoa in 2003. She completed her doctoral dissertation in 2009 with Professor Yian Shi at Colorado State University. She is currently a postdoctoral fellow in Professor Christopher Ackerson's laboratory working on the synthesis of monodispersed thiolate-protected gold nanoparticles at Colorado State University.

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Processing of cyclopropylarenes by toluene dioxygenase: isolation and absolute configuration of metabolites

Cited by 10 publications

References 12 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.

Cycloadditions of Alkenylboronic Derivatives

A novel class of tunable cyclopropanation reagents (RXZnCH2Y) and their synthetic applications

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