Cyclo[-His-His-] derived C2-symmetric diketopiperazine as chiral ligand for asymmetric diels-alder reactions

Masahiro Furutani; Seiji Sakamoto; Kazuaki Kudo

doi:10.3987/COM-08-11604

Cyclo[-His-His-] derived C₂-symmetric diketopiperazine as chiral ligand for asymmetric diels-alder reactions

Masahiro Furutani, Seiji Sakamoto, Kazuaki Kudo

Division of Organic- and Biomaterials Research

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

A cyclic dipeptide based chiral ligand, cyclo[-His(Tr)-His(Tr)-] (Tr = triphenylmethyl), was designed and prepared through bis-(τ)-tritylation of two imidazole rings of cyclo[-His-His-]. The complex prepared in situ by mixing Cu(OTf)₂ with equimolar amount of this ligand successfully catalyzed asymmetric Diels-Alder reactions in fair to good yields and moderate selectivities.

Original language	English
Pages (from-to)	1171-1176
Number of pages	6
Journal	Heterocycles
Volume	78
Issue number	5
DOIs	https://doi.org/10.3987/COM-08-11604
Publication status	Published - 2009 May 1

Keywords

Bidentate Ligand
Cu-Gatalyzed Reaction
Cyclic Dipeptide
Enantioselectivity

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-08-11604

Cite this

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title = "Cyclo[-His-His-] derived C2-symmetric diketopiperazine as chiral ligand for asymmetric diels-alder reactions",

abstract = "A cyclic dipeptide based chiral ligand, cyclo[-His(Tr)-His(Tr)-] (Tr = triphenylmethyl), was designed and prepared through bis-(τ)-tritylation of two imidazole rings of cyclo[-His-His-]. The complex prepared in situ by mixing Cu(OTf)2 with equimolar amount of this ligand successfully catalyzed asymmetric Diels-Alder reactions in fair to good yields and moderate selectivities.",

keywords = "Bidentate Ligand, Cu-Gatalyzed Reaction, Cyclic Dipeptide, Enantioselectivity",

author = "Masahiro Furutani and Seiji Sakamoto and Kazuaki Kudo",

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T1 - Cyclo[-His-His-] derived C2-symmetric diketopiperazine as chiral ligand for asymmetric diels-alder reactions

AU - Furutani, Masahiro

AU - Sakamoto, Seiji

AU - Kudo, Kazuaki

PY - 2009/5/1

Y1 - 2009/5/1

N2 - A cyclic dipeptide based chiral ligand, cyclo[-His(Tr)-His(Tr)-] (Tr = triphenylmethyl), was designed and prepared through bis-(τ)-tritylation of two imidazole rings of cyclo[-His-His-]. The complex prepared in situ by mixing Cu(OTf)2 with equimolar amount of this ligand successfully catalyzed asymmetric Diels-Alder reactions in fair to good yields and moderate selectivities.

AB - A cyclic dipeptide based chiral ligand, cyclo[-His(Tr)-His(Tr)-] (Tr = triphenylmethyl), was designed and prepared through bis-(τ)-tritylation of two imidazole rings of cyclo[-His-His-]. The complex prepared in situ by mixing Cu(OTf)2 with equimolar amount of this ligand successfully catalyzed asymmetric Diels-Alder reactions in fair to good yields and moderate selectivities.

KW - Bidentate Ligand

KW - Cu-Gatalyzed Reaction

KW - Cyclic Dipeptide

KW - Enantioselectivity

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JF - Heterocycles

SN - 0385-5414

IS - 5

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