Domino [Pd]-Catalysis: One-Pot Synthesis of Isobenzofuran-1(3<i>H</i>)-ones

Mahendar, Lodi; Satyanarayana, Gedu

doi:10.1021/acs.joc.6b01396

Cited by 45 publications

(21 citation statements)

References 69 publications

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“…1-(3 H)-Isobenzofuranone or phthalide skeletons are known for various biological activitiesa nd are present in al arge number of natural products and pharmaceuticals. [18] Isobenzofuranones are also used as precursors for the synthesis of functionalized anthracenes,n aphthalenes, and naphthacene-based natural products. [11b] Additionally,i sobenzofuranones are also known for the production of as pecial type of polymers, which have high heat resistance capacity.…”

Section: Resultsmentioning

confidence: 99%

Solvent‐free, l‐Leucine‐Catalyzed Direct Dehydrative Esterification of Carboxylic Acids with Alcohols: Direct Synthesis of 3‐Alkoxy 1(3 H)‐isobenzofuranone

et al. 2017

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Al -leucine-catalyzed mild and efficient method has been developed for the synthesis of open-chain as well as cyclic esters. Aw ider ange of alcohols, including primary, secondary,a nd tertiaryw ith aliphatic and aromatic side chains, were successfully tolerated. In the case of 2-carboxybenzaldehydes with different alcohols, 3-alkoxy-1-(3 H)-isobenzofuranones were obtained in good yields. Alcohols from natural origin have also been reacted with various acids successfully to get the corresponding esters. The reaction proceeded under neat conditions and there is no need for any acid, base, or removal of water during the reaction.

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Section: Resultsmentioning

confidence: 99%

Solvent‐free, l‐Leucine‐Catalyzed Direct Dehydrative Esterification of Carboxylic Acids with Alcohols: Direct Synthesis of 3‐Alkoxy 1(3 H)‐isobenzofuranone

et al. 2017

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“…assembling biorelevant heterocycles, a series of follow‐up transformations were demonstrated (Scheme 1). For instance, isobenzofuranone 4 was synthesized from ( R )‐ 1 a in just one step by palladium‐catalyzed carbonylation (63 % yield, 94 % ee ) [20] . In addition, a versatile chiral amino alcohol 5 was readily obtained from ( R )‐ 1 a and ammonia by Ullmann‐type amination in 75 % yield and 92 % ee [21] .…”

Section: Figurementioning

confidence: 99%

“…For instance, isobenzofuranone 4 was synthesized from (R)-1 a in just one step by palladiumcatalyzed carbonylation (63 % yield, 94 % ee). [20] In addition, a versatile chiral amino alcohol 5 was readily obtained from (R)-1 a and ammonia by Ullmann-type amination in 75 % yield and 92 % ee. [21] To our delight, 5 could be further transformed into a variety of chiral heterocycles.…”

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confidence: 99%

Kinetic Resolution of Tertiary Benzyl Alcohols via Palladium/Chiral Norbornene Cooperative Catalysis

Liu

Xie

et al. 2021

Angewandte Chemie

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Herein we report a highly enantioselective kinetic resolution of tertiary benzyl alcohols via palladium/chiral norbornene cooperative catalysis. With simple aryl iodides as the resolution reagent, a wide range of readily available racemic tertiary benzyl alcohols are applicable to this method. Both chiral tertiary benzyl alcohols and benzo[c]chromene products are obtained in good to excellent enantioselectivities (selectivity factor up to 544). The appealing synthetic utility of the obtained enantioenriched tertiary alcohols is demonstrated by the facile preparation of several valuable chiral heterocycles. Preliminary mechanism studies include DFT calculations to explain the origin of enantiodiscrimination and control experiments to uncover the formation of a transient axial chirality during the kinetic resolution step.

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“…Against this background we investigated the potential of P450 BM3 for the stereoselective hydroxylation of benzoic acid derivatives, to give access to optically active phthalides and isocoumarins. Chiral phthalides and isocoumarins often exist as natural products with different biological activities, and various methods for enantioselective synthesis of these chiral lactones have been reported . However, chemical access through stereoselective hydroxylation has not been addressed.…”

Section: Introductionmentioning

confidence: 99%

P450 BM3‐Catalyzed Regio‐ and Stereoselective Hydroxylation Aiming at the Synthesis of Phthalides and Isocoumarins

et al. 2017

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Cytochrome P450 BM3 monooxygenases are able to catalyze the regio- and stereoselective oxygenation of a broad range of substrates, with promising potential for synthetic applications. To study the suitability of P450 BM3 variants for stereoselective benzylic hydroxylation of 2-alkylated benzoic acid esters, the biotransformation of methyl 2-ethylbenzoate, resulting in both enantiomeric forms of 3-methylphthalide, was investigated. In the case of methyl 2-propylbenzoate as a substrate the regioselectivity of the reaction was shifted towards β-hydroxylation, resulting in the synthesis of enantioenriched R- and S-configured 3-methylisochroman-1-one. The potential of P450 BM3 variants for regio- and stereoselective synthesis of phthalides and isocoumarins offers a new route to a class of compounds that are valuable synthons for a variety of natural compounds.

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Domino [Pd]-Catalysis: One-Pot Synthesis of Isobenzofuran-1(3H)-ones

Cited by 45 publications

References 69 publications

Solvent‐free, l‐Leucine‐Catalyzed Direct Dehydrative Esterification of Carboxylic Acids with Alcohols: Direct Synthesis of 3‐Alkoxy 1(3 H)‐isobenzofuranone

Solvent‐free, l‐Leucine‐Catalyzed Direct Dehydrative Esterification of Carboxylic Acids with Alcohols: Direct Synthesis of 3‐Alkoxy 1(3 H)‐isobenzofuranone

Kinetic Resolution of Tertiary Benzyl Alcohols via Palladium/Chiral Norbornene Cooperative Catalysis

P450 BM3‐Catalyzed Regio‐ and Stereoselective Hydroxylation Aiming at the Synthesis of Phthalides and Isocoumarins

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