Photodecarboxylative additions of N-protected α-amino acids to N-methylphthalimide

Gallagher, Sonia; Hatoum, Fadi; Zientek, Nicolai; Oelgemöller, Michael

doi:10.1016/j.tetlet.2010.05.020

Cited by 21 publications

(6 citation statements)

References 38 publications

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“…The acetone-sensitised photodecarboxylation chemistry initially developed by Griesbeck [58] under batch conditions was suggested as being ideally suited to microflow conditions [59–60]. The chemistry involves the decarboxylative addition of potassium carboxylates to phthalimides, thus offering an alternative to Grignard reagents that can be employed under aqueous conditions [58].…”

Section: Reviewmentioning

confidence: 99%

Flow photochemistry: Old light through new windows

Knowles

Elliott²,

Booker‐Milburn³

2012

Beilstein J. Org. Chem.

361

190

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SummarySynthetic photochemistry carried out in classic batch reactors has, for over half a century, proved to be a powerful but under-utilised technique in general organic synthesis. Recent developments in flow photochemistry have the potential to allow this technique to be applied in a more mainstream setting. This review highlights the use of flow reactors in organic photochemistry, allowing a comparison of the various reactor types to be made.

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Section: Reviewmentioning

confidence: 99%

Flow photochemistry: Old light through new windows

Knowles

Elliott²,

Booker‐Milburn³

2012

Beilstein J. Org. Chem.

361

190

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“…17 Using photoinduced decarboxylation initiated by the phthalimide chromophore, Griesbeck et al developed synthetic methods for the preparation of medium and large-cyclic ethers 18 and cyclic peptides, 19 and developed novel chiral photocages. 20 Later, Oelgemöller et al used photoinduced decarboxylation for the acetate, 21 benzyl, 22 or α-amino acid addition to the phthalimide, 23 or for the formation of cyclic aryl ethers, 24 which was also conducted in the microflow reactors. 25 We have recently demonstrated that photoinduced decarboxylation of 3-(Nphthalimi-do)-1-adamantane carboxylic acid initiate addition of the photogenerated radical to electron deficient alkenes.…”

Section: Introductionmentioning

confidence: 99%

Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives

Sohora¹,

Ramljak²,

Mlinarić‐Majerski³

et al. 2014

Croat. Chem. Acta

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Abstract. New dipeptide derivatives 1 and 3 were synthesized and their reactivity in the photochemical reaction of decarboxylation was investigated. The photodecarboxylation of N-adamantyl derivatives 1a and 1b and N-phenylphthalimide derivatives 3a and 3b probably takes place from the triplet excited state. The triplet excited state of 1a, 3a and 3b was characterized by laser flash photolysis. N-phenylphthalimides 3a and 3b undergo 2−5 times more efficient photodecarboxylation than N-adamantylphthalimides 1a and 1b. The aminoacid residue (Phe or Gly) at the C-terminus of the dipeptide does not influence the photodecarboxylation efficiency. Product selectivity in the photoreactions is determined by the conformation of the molecules. N-phenylphthalimides with the separated electron donor (carboxylate) and acceptor moiety (phthalimide) give only simple decarboxylation products, whereas N-adamantyl derivatives also give cyclization products.

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“…As a result, the corresponding addition product 7e was obtained in a somewhat lower yield of 23%. N-Acyl protected amino acids successfully undergo photodecarboxylative additions with 5 (Scheme 4) [29]. A selection of these reactions was thus performed with the amino acid derivatives 8a-e in the microreactor and compared to analogue reactions conducted in the conventional chamber reactor (Table 3).…”

Section: Intermolecular Photodecarboxylative Addition Reactionsmentioning

confidence: 99%

Microflow Photochemistry—Photodecarboxylations in Microformats

2014

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This article summarizes selected examples of intra-and intermolecular photodecarboxylations involving phthalimides in a commercially available dwell device. Compared to batch conditions in a larger chamber reactor, the investigated transformations in the microreactor furnished higher conversions and yields after significantly shorter reaction times. The product qualities were commonly higher under flow conditions thus avoiding the need for further purifications.

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Photodecarboxylative additions of N-protected α-amino acids to N-methylphthalimide

Cited by 21 publications

References 38 publications

Flow photochemistry: Old light through new windows

Flow photochemistry: Old light through new windows

Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives

Microflow Photochemistry—Photodecarboxylations in Microformats

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