Cheol-Min Yook, Heesung Eum, Hyun-Joon Ha,* Kyung Yeon Kang,‡ and Won Koo Lee‡,*

 

The synthetic utility of nitrogen containing three-membered ring, aziridine1, stems from the ring-opening reaction toward acyclic α- or β-amines or ring expanded heterocycles.2 The regioselectivity of this reaction is one of the most essential elements of their synthetic values. The origin of ring openings or ring expansion reactions of aziridines is the ring strain which is quite similar to cyclopropane and oxirane when the ring nitrogen has hydrogen.1 However, the characteristics and the ring strain of aziridine depend on the substituents at the aziridine-ring nitrogen.3 The aziridine ring bearing electron withdrawing substituent, so called activated aziridine, is quite labile to the incoming nucleophiles. Unactivated aziridine is stabilized by the electron-donating substituent at the ring nitrogen with the resistance to the reaction with nucleophiles for the ring-opening reactions. Thereby, proper activation is needed to carry out the reaction of unactivated aziridines, and often made through chelation with Lewis acid or bond formation with acyl, trimethylsilyl, protonyl or alkyl group toward aziridinium ion.

1.png

 

List of Articles
번호 제목 글쓴이 날짜 조회 수
88 88. Atom Economical Synthesis of Oxindoles by Metal-Catalyzed Intramolecular C-C Bond Formation under Solvent-Free and Aerobic Conditions, Green Chem., 2015, 17, 3306–3309 imagefile aziridine 2016-03-18 1461
87 87. N-Methylative aziridine ring opening: Asymmetric synthesis of hygroline, pseudohygroline, and hygrine, Tetrahedron Letters 56 (2015) 856–858 imagefile aziridine 2016-03-18 1404
86 86. One-pot Solvent-Free Reductive Amination with a Solid Ammonium Carbamate Salt from CO2 and Amine, RSC Adv., 2014, 4, 46203–46207 imagefile aziridine 2016-03-18 1344
85 85. Asymmetric Synthesis of Fluoroamines from Chiral Aziridines, Bull. Korean Chem. Soc. 2014, Vol. 35, No. 3 file aziridine 2016-03-18 1749
84 84. Synthesis and Biological Activities of Tyroscherin Analogs, Bull. Korean Chem. Soc. 2013, Vol. 34, No. 6 file aziridine 2016-03-18 1269
83 83. Highly Stereoselective Directed Reactions and an Efficient Synthesis of Azafuranoses from a Chiral Aziridine, Org Biomol Chem. 2013 Jun 14;11(22):3629-34 imagefile aziridine 2016-03-18 1058
82 82. CAL-B catalyzed desymmetrization of 3-alkylglutarate: "olefin effect" and asymmetric synthesis of pregabalin, Org. Biomol. Chem., 2013, 11, 3635 imagefile aziridine 2013-08-27 2351
81 81. Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine, Org. Biomol. Chem., 2013, 11, 3629 imagefile aziridine 2013-08-27 2393
80 80. Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine, Tetrahedron Lett., 2013, 54, 553 imagefile aziridine 2013-08-27 2155
79 79. Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine, Tetrahedron Lett., 2013, 54, 1384 imagefile aziridine 2013-08-27 2194
78 78. Chemoselective reduction of olefin by mixed "Pd" catalyst, Bulletin of the Korean Chemical Society (2012), 33(9), 2853-2854. imagefile aziridine 2013-05-30 2451
77 77. Highly improved copper-mediated Michael addition of ethyl bromodifluoroacetate in the presence of protic additive, Synthesis (2012), 44(20), 3165-3170. imagefile aziridine 2013-05-30 1808
76 76. The sphingosine-1-phosphate derivative NHOBTD inhibits angiogenesis both in vitro and in vivo, Biochemical and biophysical research communications (2011), 413(2), 189-93. file aziridine 2013-05-30 1769
75 75. Synthesis of 2,5-Disubstituted 6-Azaindoles from Substituted Aziridines via Intramolecular Cyclization, ORGANIC LETTERS, 2012, Vol. 14, No. 12, 3120–3122. imagefile aziridine 2012-06-11 2355
74 74. Alkylative Ring Opening of N-Methylaziridinium Ions and a Formal Synthesis of Tyroscherin, Org. Lett., 2012, Vol. 14, No. 2, 429–431 imagefile aziridine 2012-06-11 2397
73 73. Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines, Org. Biomol. Chem., 2011, 9, 1372 imagefile aziridine 2012-01-27 3023
72 72. Chiral aziridine-2-carboxylates: versatile precursors for functionalized tetrahydroisoquinoline (THIQ) containing heterocycles, Tetrahedron 68 (2012) 883-893 imagefile aziridine 2012-01-27 2803
71 71. 3,4-Disubstituted oxazolidin-2-ones as constrained ceramide analogs with anticancer activities. Bioorganic & Medicinal Chemistry 19 (2011) 6174–6181 imagefile aziridine 2012-01-27 3114
70 70. N-Methylative aziridine ring opening and asymmetric synthesis of MeBmt. Tetrahedron Letters 52 (2011) 5918–5920 imagefile aziridine 2012-01-27 3044
» 69. Regiochemical Pathway in the Ring Opening of 2-Acylaziridines. Bull. Korean Chem. Soc. 2011, Vol. 32, No. 8 2879 imagefile aziridine 2012-01-27 3154
68 68. Synthesis of 1,2,5-and 1,2,3,5-substituted pyrroles from substituted aziridines via Ag(I)-catalyzed intramolecular cyclization , Tetrahedron 67 (2011) 3553-3556. imagefile aziridine 2011-05-06 3776
67 67. Aminostyrylbenzofuran derivatives as potent inhibitors for Aβ fibril formation-BMCL, 2008, 18, 5591-5593 imagefile aziridine 2010-09-27 4569
66 66. An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines - Tetrahedron, 2010, 66, 8108-8114 imagefile aziridine 2010-09-08 4495
65 65. A formal synthesis of (-)-swainsonine from a chiral aziridine - Tetrahedron Lett. 2010, 51, 3284 imagefile aziridine 2010-05-29 4830
64 64. Conjugate addition of amines to chiral 3-aziridin-2-yl-acrylates - Tetrahedron Lett. 2010, 2181 imagefile aziridine 2010-05-29 4896
63 63. Synthesis of substituted imidazolidin-2-ones as aminoacyl-tRNA synthase inhibitors - Bull.Kor.Chem.Soc. 2010, 611 imagefile aziridine 2010-05-29 4668
62 62. Molecular docking study of aminoacyl-tRNA synthetases with ligand molecules from four different scaffolds - Bull.Kor.Chem.Soc 2010, 606 imagefile aziridine 2010-05-29 4198
61 61. Molecular basis for the stereoselective ammoniolysis of N-alkyl aziridine-2-carboxylates catalyzed by Candida antarctica lipase B - ChemBioChem 2009, 10, 2213 imagefile aziridine 2010-05-29 4478
60 60. Synthesis of D-erythro-sphingosine from D-ribo-phytosphingoshine - Bull. Kor. Chem. Soc. 2009, 535 imagefile aziridine 2010-05-29 4254
59 59. [Synthetic ceramide analogs for anticancer agents] in Glycolipids New Research, Nova Science Pub. New York, 2008, 145- 156 imagefile aziridine 2010-05-29 4589


XE Login