Methyl 2‐(Benzyloxycarbonylamino)‐2‐cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl‐Containing Amino Acids

Limbach, Michael; Lygin, Alexander V.; Es‐Sayed, Mazen; Meijere, Armin de

doi:10.1002/ejoc.200800817

Cited by 6 publications

(2 citation statements)

References 33 publications

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“…As depicted in Scheme , the synthesis of aminomethylenecyclopropanes has been achieved from the cyclopropanecarbaldehydes by aminal formation and subsequent rearrangement into A by heating 6. For the synthesis of nucleoside analogues, Somekawa and Zemlicka independently reported the use of 1‐bromo‐1‐(bromomethyl)cyclopropane for an N ‐alkylation, followed by an in situ β‐elimination 7,8. Herein, we report an alternative approach for the synthesis of aminomethylenecyclopropane A using a palladium‐mediated [2+1] cycloaddition between an activated alkene and an ynamide partner 9…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides

Clavier¹,

Lepronier²,

Bengobesse‐Mintsa³

et al. 2013

Adv Synth Catal

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International audienceAn efficient palladium-catalyzed [2 + 1]cycloaddition between ynamides and norbornenes or norbornadienes is reported. Both phosphapalla- dacycles and palladium/secondary phosphine oxide catalytic systems were found to be competent for the transformation allowing the preparation of ami- nomethylenecyclopropanes. The reaction showed general applicability to various functionalized bicyclo[2.2.1]hept-2-enes and ynamides. A chiral phosphapalladacycle was tested to carry out this transformation in an enantioselective fashion

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Section: Methodsmentioning

confidence: 99%

Palladium‐Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides

Clavier¹,

Lepronier²,

Bengobesse‐Mintsa³

et al. 2013

Adv Synth Catal

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“…Methylenecyclopropane and its derivatives1 are endowed with enhanced reactivities across their double bonds2 as well as their three‐membered rings,3 and this has been utilized in a multitude of synthetically useful transformations. With an electron‐withdrawing group attached to the double bond such as in an alkyl 2‐cyclopropylideneacetate,4 a dialkyl cyclopropylidenemalonate,5 methyl 2‐(benzyloxycarbonylamino)‐2‐cyclopropylideneacetate,6 an alkyl 2‐bromo‐2‐cyclopropylideneacetate7 or an alkyl 2‐chloro‐2‐cyclopropylideneacetate such as 1 ,8 methylenecyclopropanes are particularly good dienophiles as well as Michael acceptors.…”

Section: Introductionmentioning

confidence: 99%

Versatile Access to 2‐Aminocyclobutene‐1‐carboxylic Acid Derivatives and Their Incorporation into Small Peptides

Meijere¹,

Limbach²,

Janssen³

et al. 2010

Eur J Org Chem

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Under a newly developed set of mild conditions [EtN(iPr) 2 , LiI, DMF, 20°C, 3 d], methyl 2-chloro-2-cyclopropylideneacetate (1) smoothly undergoes Michael addition of various benzylamines (4 examples) with ensuing ring enlargement and elimination to give in very good yields (81-99 %) the correspondingly substituted methyl 2-(benzylamino)cyclobutenecarboxylates 3a-d, which were subsequently converted into the N-Boc-protected derivatives 4a-d. After hydrolysis of the esters, the free β-amino acids 5a,b were cleanly condensed with the methyl esters of gly-

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[2+1] Cycloaddition Affording Methylene- and Vinylidenecyclopropane Derivatives: A Journey around the Reactivity of Metal-Phosphinito-Phosphinous Acid Complexes

Clavier

Buono

2016

Chem. Rec.

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Metal-phosphinito-phosphinous acid complexes are interesting catalysts exhibiting unique reactivities. In this account, we intend to provide a clear overview of palladium- and platinum-phosphinito-phosphinous acid complexes, their preparation from secondary phosphine oxides, and their applications in catalysis. They have been mainly used to develop [2+1] cycloadditions to afford methylenecyclopropane derivatives using norbornenes and various alkynes as partners. As a function of the catalyst, the reaction conditions, or the nature of the reagents, different synthetic transformations have been observed: [2+1] cycloadditions, giving rise to either alkylidenecyclopropanes or vinylidenecyclopropanes; tandem [2+1]/[3+2] cycloadditions, and so forth. The mechanisms of these reactions have been studied to rationalize the different reactivities observed.

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Methyl 2‐(Benzyloxycarbonylamino)‐2‐cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl‐Containing Amino Acids

Cited by 6 publications

References 33 publications

Palladium‐Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides

Palladium‐Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides

Versatile Access to 2‐Aminocyclobutene‐1‐carboxylic Acid Derivatives and Their Incorporation into Small Peptides

[2+1] Cycloaddition Affording Methylene- and Vinylidenecyclopropane Derivatives: A Journey around the Reactivity of Metal-Phosphinito-Phosphinous Acid Complexes

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