2015
DOI: 10.1021/acs.orglett.5b02810
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Silver(I)-Catalyzed Enantioselective Desymmetrization of Cyclopentenediones: Access to Highly Functionalized Bicyclic Pyrrolidines

Abstract: A highly enantioselective desymmetrization of prochiral cyclopentenediones via Ag(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylide has been developed successfully. The methodology performs well over a broad scope of substrates, which provides facile access to a series of highly functionalized bicyclic pyrrolidine/cyclopentane derivatives in good to high yields with excellent stereoselectivities.

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Cited by 54 publications
(12 citation statements)
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“…Ag(I)/TF-BiphamPhos-catalyzed [3 + 2] cycloaddition of cyclopentene-1,3-diones with azomethine ylide. [39] subsequent ring-closing nucleophilic addition provided the intermediate 83, which went through further aromatization and methylation to provide the desired product 72.…”
Section: Desymmetrization Via Cycloaddition Reactionmentioning
confidence: 99%
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“…Ag(I)/TF-BiphamPhos-catalyzed [3 + 2] cycloaddition of cyclopentene-1,3-diones with azomethine ylide. [39] subsequent ring-closing nucleophilic addition provided the intermediate 83, which went through further aromatization and methylation to provide the desired product 72.…”
Section: Desymmetrization Via Cycloaddition Reactionmentioning
confidence: 99%
“…Wang and co‐workers successfully reported the same type of [3+2] cycloaddition of prochiral cyclopentene‐1,3‐diones ( 1 ) with azomethine ylide ( 46 ) by using Ag(I)/TF‐BiphamPhos ( L14 ) for the synthesis of bicyclic‐pyrrolidine derivatives ( 47 ) via enantioselective desymmetrization protocol under mild reaction condition (Scheme 13). [39] Synthesis of highly functionalized enantioenriched bicyclic‐cyclopentane/pyrrolidine was very well explained through 1,3 dipolar cycloaddition of azomethine ylide with excellent yield and diastereoselectivity. The generality of the developed methodology was tested by using a series of electron‐withdrawing and donating groups substituted in the aromatic ring of azomethine ylide as well as several 2,2 disubstituted cyclopentene‐1,3‐diones and in most of the cases, the desired bicyclic‐pyrrollidines were obtained with excellent yield (up to 93 %), excellent enantioselectivity (up to 99 %) and diastereoselectivity (>20 : 1).…”
Section: Desymmetrization Via Cycloaddition Reactionmentioning
confidence: 99%
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“…The reaction was performed at -20 °C afford-ing products 237 in good yields and high optical purities (up to >99 ee) (Scheme 69). 103 Bicyclic heterocycles fused by pyrrolidine and cyclopentane moieties play a unique role in numerous bioactive naturally occurring compounds and pharmaceutical ingredients. This chiral catalytic complex was also employed for atroposelective desymmetrization of N-(2-tert-butylphenyl)maleimides during an enantioselective 1,3-DC affording enantiomerically pure cycloadducts 239, which could be transformed into pyrrolines (e.g., 240) and pyrroles (e.g.…”
Section: Scheme 67 Synthesis Of Pyrrolo[34-c]pyrrolesmentioning
confidence: 99%
“…Transition-metal-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethineylides has doubtlessly been one of the most ideal and powerful synthetic strategies for assembly of structurally diverse pyrrolidines . Since the pioneering work by Grigg, an enormous number of ligands, which are crucial in an enantioselective bond forming process, have been developed to achieve these reactions, including Wang’s TF-Biphamphos, Carretereo’s Fe-sulphos, Zhang’s Ming-Phos, Fukuzawa’s ThioClickFerrophos, Xu’s Xing-Phos, and so on. Despite these impressive advances, the design and synthesis of structurally novel and highly efficient P-stereogenic ligands for enantioselective catalysis is greatly desired.…”
mentioning
confidence: 99%