A novel one-pot reaction involving organocopper-mediated reduction/transmetalation/asymmetric alkylation, leading to the diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres

被引：29

作者：

Narumi, Tetsuo

Niida, Ayumu

Tomita, Kenji

Oishi, Shinya

Otaka, Akira

Ohno, Hiroaki

Fujii, Nobutaka ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

来源：

CHEMICAL COMMUNICATIONS | 2006年 / 45期

关键词：

D O I：

10.1039/b608596b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By a novel one-pot reaction sequence involving consecutive organocopper-mediated reduction, transmetalation and asymmetric alkylation, a highly diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres was achieved in good to excellent yields.

引用

页码：4720 / 4722

页数：3

共 8 条

[1] Development of diastereoselective synthetic strategy toward (Z)-fluoroalkene dipeptide isosteres based on organocopper-mediated reduction/direct alkylation via transmetalation
Narumi, T.
Tomita, K.
Niida, A.
Oishi, S.
Ohno, H.
Fujii, N.
JOURNAL OF PEPTIDE SCIENCE, 2006, 12 : 114 - 114
[2] Synthesis of (Z)-fluoroalkene dipeptide isosteres utilizing organocopper-mediated reduction of γ,γ-difluoro-α,β-enoates
Otaka, A
Watanabe, H
Mitsuyama, E
Yukimasa, A
Tamamura, H
Fujii, N
TETRAHEDRON LETTERS, 2001, 42 (02) : 285 - 287
[3] Diastereoselective synthesis of ψ[(E)-CH=CMe]- and ψ[(Z)-CH=CMe]-type dipeptide isosteres by organocopper-mediated anti-SN2′ reaction
Oishi, S
Kamano, T
Niida, A
Odagaki, Y
Tamamura, H
Otaka, A
Hamanaka, N
Fujii, N
ORGANIC LETTERS, 2002, 4 (07) : 1051 - 1054
[4] Diastereoselective synthesis of ψ[(E)-CMe=CH]- and ψ[(E)-CMe=CMe]-type dipeptide isosteres based on organocopper-mediated anti-SN2′ reaction
Oishi, S
Niida, A
Kamano, T
Odagaki, Y
Tamamura, H
Otaka, A
Hamanaka, N
Fujii, N
ORGANIC LETTERS, 2002, 4 (07) : 1055 - 1058
[5] SmI2-mediated reduction of γ,γ-difluoro-α,β-enoates with application to the synthesis of functionalized (Z)-fluoroalkene-type dipeptide isosteres
Otaka, A
Watanabe, J
Yukimasa, A
Sasaki, Y
Watanabe, H
Kinoshita, T
Oishi, S
Tamamura, H
Fujii, N
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (05): : 1634 - 1645
[6] Synthesis of (Z)-alkene and (E)-fluoroalkene-containing diketopiperazine mimetics utilizing organocopper-mediated reduction-alkylation and diastereoselectivity examination using DFT calculations
Niida, Ayumu
Mizumoto, Makiko
Narumi, Tetsuo
Inokuchi, Eriko
Oishi, Shinya
Ohno, Hiroaki
Otaka, Akira
Kitaura, Kazuo
Fujii, Nobutaka
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11): : 4118 - 4129
[7] Enantio- and Diastereoselective Synthesis of Piperidines by Coupling of Four Components in a "One-Pot" Sequence Involving Diphenylprolinol Silyl Ether Mediated Michael Reaction
Urushima, Tatsuya
Sakamoto, Daisuke
Ishikawa, Hayato
Hayashi, Yujiro
ORGANIC LETTERS, 2010, 12 (20) : 4588 - 4591
[8] Lewis Acid Mediated One-Pot Synthesis of Aryl/Heteroaryl-Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence
Sureshbabu, Radhakrishnan
Saravanan, Velu
Dhayalan, Vasudevan
Mohanakrishnan, Arasambattu K.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 922 - 935

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