Catalytic Asymmetric Ring-Opening of meso-Aziridines with Malonates under Heterodinuclear Rare Earth Metal Schiff Base Catalysis

被引：94

作者：

Xu, Yingjie ^{[1
]}

Lin, Luqing ^{[1
]}

Kanai, Motomu ^{[1
]}

Matsunaga, Shigeki ^{[1
]}

Shibasaki, Masakatsu ^{[2
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

[2] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 15期

关键词：

ENANTIOSELECTIVE DESYMMETRIZATION; BIFUNCTIONAL CATALYSIS; LEWIS-ACIDS; COMPLEX; EPOXIDES; TMSN3; ACYLAZIRIDINES; STEREOCENTERS; CONSTRUCTION; FOLDAMERS;

D O I：

10.1021/ja201492x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric ring-opening of meso-aziridines with malonates is described. The combined use of two rare earth metal sources with different properties promoted the desired ring-opening reaction. A 1:1:1 mixture of a heterobimetallic La(O-iPr)(3)/Yb(OTf)(3)/Schiff base la (0.25-10 mol %) efficiently promoted the reaction of five-, six-, and seven-membered ring cyclic meso-aziridines as well as acyclic meso-aziridines with dimethyl, diethyl, and dibenzyl malonates, giving chiral cyclic and acyclic gamma-amino esters in 99-63% yield and > 99.5-97% ee.

引用

页码：5791 / 5793

页数：3

共 44 条

[1] Catalysis of the Michael addition reaction by late transition metal complexes of BINOL-derived salens
Annamalai, V
DiMauro, EF
Carroll, PJ
Kozlowski, MC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1973 - 1981
[2] The development of scalemic multidentate niobium complexes as catalysts for the highly stereoselective ring opening of meso-epoxides and meso-aziridines
Arai, Kenzo
Lucarini, Simone
Salter, Matthew M.
Ohta, Kentaro
Yamashita, Yasuhiro
Kobayashi, Shuj
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) : 8103 - 8111
[3] Construction of three contiguous tertiary stereocenters from Aziridines in one step
Blyumin, Evgeniy V.
Gallon, Helen J.
Yudin, Andrei K.
[J]. ORGANIC LETTERS, 2007, 9 (23) : 4677 - 4680
[4] Bryans JS, 1999, MED RES REV, V19, P149, DOI 10.1002/(SICI)1098-1128(199903)19:2<149::AID-MED3>3.0.CO
[5] 2-B
[6] Enantioselective Michael reaction of 1,3-dicarbonyl compounds to 3-nitro-2H-chromenes catalyzed by chiral nickel complexes
Chen, Wei-Yi
Ouyang, Luo
Chen, Rui-Ye
Li, Xin-Sheng
[J]. TETRAHEDRON LETTERS, 2010, 51 (30) : 3972 - 3974
[7] Cooper JR., 2003, The biochemical basis of neuropharmacology, V8th
[8] Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of meso-Aziridines
Della Sala, Giorgio
Lattanzi, Alessandra
[J]. ORGANIC LETTERS, 2009, 11 (15) : 3330 - 3333
[9] Orthogonal Lewis acids: Catalyzed ring opening and rearrangement of acylaziridines
Ferraris, D
Drury, WJ
Cox, C
Lectka, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (14) : 4568 - 4569
[10] Key role of the Lewis base position in asymmetric bifunctional catalysis: Design and evaluation of a new ligand for chiral polymetallic catalysts
Fujimori, Ikuo
Mita, Tsuyoshi
Maki, Keisuke
Shiro, Motoo
Sato, Akihiro
Furusho, Sanae
Kanai, Motomu
Shibasaki, Masakatsu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) : 16438 - 16439

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