Enhanced Diastereoselectivity in the Asymmetric Ugi Reaction Using a New “Convertible” Isonitrile

Linderman, Russell J.; Binet, Sophie; Petrich, Samantha R.

doi:10.1021/jo982186e

Cited by 96 publications

(35 citation statements)

References 14 publications

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“…To facilitate the final hydrolysis of product 70, 2-(tert-butyldimethylsilyloxymethyl)phenylisocyanide (R 2 NC in Scheme 30) was introduced; the excellent results of the Ugi reaction were maintained. [115] The related 2,3,4-tri-O-pivaloyl-a-d-arabinosylamine was introduced successfully instead of chiral amine 5 to obtain the amino acids with S configuration. [116] An interesting variant of Ugi four-component reaction was developed with an a-amino acid as the amine partner and with an alcohol instead of the carboxylic acid.…”

Section: Four-component Approachmentioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.

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Section: Four-component Approachmentioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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“…Moreover, probably, the Lewis acid favors direct attack of the isonitrile (mechanism A of Scheme 1.9). The substantial independence of the stereoselectivity from the structure of the aldehyde makes this methodology extremely convenient to prepare d-amino acid derivatives [35]. It has also been used for solid-phase syntheses [36].…”

Section: Glycosylaminesmentioning

confidence: 99%

Asymmetric Isocyanide‐Based MCRs

Banfi

Basso

Guanti

et al. 2005

Multicomponent Reactions

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“…[4] Today, MCRs represent ideal strategies for the preparation of complex structures from unstable and inseparable reaction intermediates and are particularly attractive for both natural product and diversity-oriented syntheses (DOS). [5] However, to date there are only a few reports of organocatalytic multicomponent Diels-Alder reactions for the synthesis of stereochemically complex compounds and of spirocyclic derivatives with quaternary carbon centers in a stereocontrolled manner.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Multicomponent α‐Methylenation/Diels–Alder Reactions: A Versatile Route to Substituted Cyclohexenecarbaldehyde Derivatives

Zou¹,

Wang²,

Goeke³

2008

Chemistry A European J

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This article describes the design and optimization of an effective organocatalytic three-component domino alpha-methylenation/Diels-Alder reaction to produce vinyl-substituted cyclohexenecarboxaldehydes in a highly regioselective fashion. In these one-pot transformations, 2-formyl-1,3-butadienes (4) were prepared in situ from alpha,beta-unsaturated aldehydes and formalin and were subsequently trapped with a variety of buta-1,3-dienes. The outcomes of the reactions were dependent on the electronic properties of the dienes. 1-Vinylcyclohexenecarbaldehydes 6 were formed by use of acyclic electron-rich dienes, while the initially formed cycloadducts of 4 with cyclopentadiene underwent Cope rearrangements, leading to the formation of tetrahydro-3H-indene-5-carbaldehyde compounds 7. The mechanisms involved in these reactions were deduced from experimental findings. Furthermore, the method was also extended to one-pot domino methylenation/Diels-Alder reactions of dihydrofurans and dihydropyrans to yield spirocyclic lactols 22. In these reactions, the unstable intermediate hydroxyethyl and hydroxypropyl acroleins behaved as dienophiles, undergoing cycloaddition reactions with dienes with good yields and selectivities. The wide variety of functionalized 1-vinylcyclohex-3-enecarbaldehydes 6, 4-vinylcyclohex-1-enecarbaldehydes 7, and spiro lactols 22 generated through the use of these organocatalytic domino processes as a diversity-oriented synthesis provided useful intermediates for the construction of novel odorants.

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Enhanced Diastereoselectivity in the Asymmetric Ugi Reaction Using a New “Convertible” Isonitrile

Cited by 96 publications

References 14 publications

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Asymmetric Isocyanide‐Based MCRs

Organocatalytic Multicomponent α‐Methylenation/Diels–Alder Reactions: A Versatile Route to Substituted Cyclohexenecarbaldehyde Derivatives

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