Enantioselective approach to indolizidine and quinolizidine scaffolds. Application to the synthesis of peptide mimics

Yuanyuan Lu; Sílvia Alujas-Burgos; Cristina Oliveras-González; Laura Vázquez-Jiménez; Pep Rojo; Ángel Álvarez-Larena; Pau Bayón; Marta Figueredo

doi:10.1016/j.tet.2017.11.042

Enantioselective approach to indolizidine and quinolizidine scaffolds. Application to the synthesis of peptide mimics

Yuanyuan Lu, Sílvia Alujas-Burgos, Cristina Oliveras-González, Laura Vázquez-Jiménez, Pep Rojo, Ángel Álvarez-Larena, Pau Bayón, Marta Figueredo

Departament de Química

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Resum

© 2017 Elsevier Ltd An enantioselective approach to substituted indolizidine and quinolizidine frameworks has been developed. Key steps of the synthesis are the enantioselective, palladium-catalyzed N-allylation of an imide, the nucleophilic allylation of an acyliminium ion and a ring closing metathesis. This general strategy has been applied to the synthesis of indolizidine peptide mimics, starting from a chiral imide derived from L-aspartic acid. It was observed that the preexisting stereogenic center of this substrate has a moderate influence on the stereoselectivity of the electrophilic allylation, which is mainly determined by the sense of chirality of the catalyst.

Idioma original	English
Pàgines (de-a)	104-116
Revista	Tetrahedron
Volum	74
Número	1
DOIs	https://doi.org/10.1016/j.tet.2017.11.042
Estat de la publicació	Publicada - 4 de gen. 2018

Accés al document

10.1016/j.tet.2017.11.042

https://ddd.uab.cat/record/182263

CCDC 1544711: Experimental Crystal Structure Determination
Lu, Y. (Creador), Alujas-Burgos, S. (Creador), Oliveras-González, C. (Creador), Vázquez-Jiménez, L. (Creador), Rojo, P. (Creador), Álvarez-Larena, Á. (Creador), Bayón, P. (Creador) & Figueredo, M. (Creador), Cambridge Crystallographic Data Centre, 18 d’abr. 2017
DOI: 10.5517/ccdc.csd.cc1nvdd9, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nvdd9&sid=DataCite
Conjunt de dades: Datasets
CCDC 1544712: Experimental Crystal Structure Determination
Lu, Y. (Creador), Alujas-Burgos, S. (Creador), Oliveras-González, C. (Creador), Vázquez-Jiménez, L. (Creador), Rojo, P. (Creador), Álvarez-Larena, Á. (Creador), Bayón, P. (Creador) & Figueredo, M. (Creador), Cambridge Crystallographic Data Centre, 18 d’abr. 2017
DOI: 10.5517/ccdc.csd.cc1nvdfb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nvdfb&sid=DataCite
Conjunt de dades: Datasets

Com citar-ho

@article{c3d4bf65d2e943fabdc611b901626a7a,

title = "Enantioselective approach to indolizidine and quinolizidine scaffolds. Application to the synthesis of peptide mimics",

abstract = "{\textcopyright} 2017 Elsevier Ltd An enantioselective approach to substituted indolizidine and quinolizidine frameworks has been developed. Key steps of the synthesis are the enantioselective, palladium-catalyzed N-allylation of an imide, the nucleophilic allylation of an acyliminium ion and a ring closing metathesis. This general strategy has been applied to the synthesis of indolizidine peptide mimics, starting from a chiral imide derived from L-aspartic acid. It was observed that the preexisting stereogenic center of this substrate has a moderate influence on the stereoselectivity of the electrophilic allylation, which is mainly determined by the sense of chirality of the catalyst.",

keywords = "Indolizidines, Peptide mimics, Quinolizidines, Steroselective synthesis",

author = "Yuanyuan Lu and S{\'i}lvia Alujas-Burgos and Cristina Oliveras-Gonz{\'a}lez and Laura V{\'a}zquez-Jim{\'e}nez and Pep Rojo and {\'A}ngel {\'A}lvarez-Larena and Pau Bay{\'o}n and Marta Figueredo",

year = "2018",

month = jan,

day = "4",

doi = "10.1016/j.tet.2017.11.042",

language = "English",

volume = "74",

pages = "104--116",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - Enantioselective approach to indolizidine and quinolizidine scaffolds. Application to the synthesis of peptide mimics

AU - Lu, Yuanyuan

AU - Alujas-Burgos, Sílvia

AU - Oliveras-González, Cristina

AU - Vázquez-Jiménez, Laura

AU - Rojo, Pep

AU - Álvarez-Larena, Ángel

AU - Bayón, Pau

AU - Figueredo, Marta

PY - 2018/1/4

Y1 - 2018/1/4

N2 - © 2017 Elsevier Ltd An enantioselective approach to substituted indolizidine and quinolizidine frameworks has been developed. Key steps of the synthesis are the enantioselective, palladium-catalyzed N-allylation of an imide, the nucleophilic allylation of an acyliminium ion and a ring closing metathesis. This general strategy has been applied to the synthesis of indolizidine peptide mimics, starting from a chiral imide derived from L-aspartic acid. It was observed that the preexisting stereogenic center of this substrate has a moderate influence on the stereoselectivity of the electrophilic allylation, which is mainly determined by the sense of chirality of the catalyst.

AB - © 2017 Elsevier Ltd An enantioselective approach to substituted indolizidine and quinolizidine frameworks has been developed. Key steps of the synthesis are the enantioselective, palladium-catalyzed N-allylation of an imide, the nucleophilic allylation of an acyliminium ion and a ring closing metathesis. This general strategy has been applied to the synthesis of indolizidine peptide mimics, starting from a chiral imide derived from L-aspartic acid. It was observed that the preexisting stereogenic center of this substrate has a moderate influence on the stereoselectivity of the electrophilic allylation, which is mainly determined by the sense of chirality of the catalyst.

KW - Indolizidines

KW - Peptide mimics

KW - Quinolizidines

KW - Steroselective synthesis

U2 - 10.1016/j.tet.2017.11.042

DO - 10.1016/j.tet.2017.11.042

M3 - Article

SN - 0040-4020

VL - 74

SP - 104

EP - 116

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Enantioselective approach to indolizidine and quinolizidine scaffolds. Application to the synthesis of peptide mimics

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Conjunts de dades

CCDC 1544711: Experimental Crystal Structure Determination

CCDC 1544712: Experimental Crystal Structure Determination

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