Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

Mostafa M. Amer; Ana C. Carrasco; Daniel J. Leonard; John W. Ward; Jonathan Clayden

doi:10.1021/acs.orglett.8b03551

Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

Mostafa M. Amer, Ana C. Carrasco, Daniel J. Leonard, John W. Ward, Jonathan Clayden^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

Imidazolidinone derivatives of a range of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler-Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C=O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones and their congeners in enantioenriched form.

Original language	English
Pages (from-to)	7977-7981
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	24
Early online date	5 Dec 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b03551
Publication status	Published - 21 Dec 2018

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@article{2b83013a1cfa4535a32ef79f16358500,

title = "Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids",

abstract = "Imidazolidinone derivatives of a range of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler-Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C=O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones and their congeners in enantioenriched form.",

author = "Amer, {Mostafa M.} and Carrasco, {Ana C.} and Leonard, {Daniel J.} and Ward, {John W.} and Jonathan Clayden",

year = "2018",

month = dec,

day = "21",

doi = "10.1021/acs.orglett.8b03551",

language = "English",

volume = "20",

pages = "7977--7981",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

AU - Amer, Mostafa M.

AU - Carrasco, Ana C.

AU - Leonard, Daniel J.

AU - Ward, John W.

AU - Clayden, Jonathan

PY - 2018/12/21

Y1 - 2018/12/21

N2 - Imidazolidinone derivatives of a range of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler-Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C=O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones and their congeners in enantioenriched form.

AB - Imidazolidinone derivatives of a range of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler-Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C=O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones and their congeners in enantioenriched form.

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U2 - 10.1021/acs.orglett.8b03551

DO - 10.1021/acs.orglett.8b03551

M3 - Article (Academic Journal)

C2 - 30516389

AN - SCOPUS:85058561077

SN - 1523-7060

VL - 20

SP - 7977

EP - 7981

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

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QUATERMAIN - Quaternary amino acids on scale for medicine and agroscience

alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

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Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

Abstract

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QUATERMAIN - Quaternary amino acids on scale for medicine and agroscience

alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

Cite this