Metal-Free Intramolecular Aziridination of Allylic Carbamates Mediated by Hypervalent Iodine Compounds

被引：28

作者：

Deng, Qing-Hai ^{[1
]}

Wang, Jing-Cui ^{[1
]}

Xu, Zhen-Jiang ^{[1
]}

Zhou, Cong-Ying ^{[2
,3
]}

Che, Chi-Ming ^{[1
,2
,3
]}

机构：

[1] Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai, Peoples R China

[2] Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Hong Kong, Hong Kong, Peoples R China

[3] Univ Hong Kong, Open Lab Chem Biol, Inst Mol Technol Drug Discovery & Synth, Hong Kong, Hong Kong, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2011年 / 18期

关键词：

aziridination; hypervalent iodine; allylic carbamate; ring opening; vicinal diamine; NITRENE TRANSFER-REACTIONS; OLEFIN AZIRIDINATION; EFFICIENT AZIRIDINATION; ASYMMETRIC AZIRIDINATION; CATALYZED AZIRIDINATION; CHLORAMINE-T; ENANTIOSELECTIVE AZIRIDINATION; ALKENE AZIRIDINATION; CHIRAL AZIRIDINES; NITROGEN-SOURCE;

D O I：

10.1055/s-0030-1260150

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical hypervalent iodine compound mediated metal-free intramolecular aziridination reaction of allylic carbamates was developed. Analytically pure aziridines were obtained in high yields by simple filtration of the reaction mixture. In situ ring opening of the aziridines provides an easy access to useful vicinal amino alcohol derivatives and diamine compounds. Up to 16% ee was obtained when chiral hypervalent iodine compound was used.

引用

页码：2959 / 2967

页数：9

共 63 条

[1] Aggarwal VK, 1998, SYNLETT, P329
[2] Nitrogen atom transfer to alkenes utilizing chloramine-T as a nitrogen source
Ando, T
Minakata, S
Ryu, I
Komatsu, M
[J]. TETRAHEDRON LETTERS, 1998, 39 (3-4) : 309 - 312
[3] Palladium(II)-promoted aziridination of olefins with bromamine T as the nitrogen transfer reagent
Antunes, AMM
Marto, SJL
Branco, PS
Prabhakar, S
Lobo, AM
[J]. CHEMICAL COMMUNICATIONS, 2001, (05) : 405 - 406
[4] 3-Acetoxyaminoquinazolinones (QNHOAc) as aziridinating agents: ring-opening of N-(Q)-substituted aziridines
Atkinson, RS
[J]. TETRAHEDRON, 1999, 55 (06) : 1519 - 1558
[5] Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate
Catino, AJ
Nichols, JM
Forslund, RE
Doyle, MP
[J]. ORGANIC LETTERS, 2005, 7 (13) : 2787 - 2790
[6] Synthesis, Structure, and Highly Efficient Copper-Catalyzed Aziridination with a Tetraaza-Bispidine Ligand
Comba, Peter
Haaf, Christina
Lienke, Achim
Muruganantham, Amsaveni
Wadepohl, Hubert
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (41) : 10880 - 10887
[7] Efficient aziridination of olefins catalyzed by a unique disilver(I) compound
Cui, Y
He, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) : 16202 - 16203
[8] Iminoiodanes and C-N bond formation in organic synthesis
Dauban, P
Dodd, RH
[J]. SYNLETT, 2003, (11) : 1571 - 1586
[9] Copper-catalyzed nitrogen transfer mediated by iodosylbenzene PhI=O
Dauban, P
Sanière, L
Tarrade, A
Dodd, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) : 7707 - 7708
[10] Organocatalytic Enantioselective Aziridination of α-Substituted α,β-Unsaturated Aldehydes: Asymmetric Synthesis of Terminal Aziridines
Deiana, Luca
Zhao, Gui-Ling
Lin, Shuangzheng
Dziedzic, Pawel
Zhang, Qiong
Leijonmarck, Hans
Cordova, Armando
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3201 - 3207

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