Yongeun Kim, Hyun-Joon Ha, Hoseop Yun, Baeck Kyoung Lee and Won Koo Lee                            

 

Good nucleophilicity of the ring nitrogen in chiral (2R,10R)-2-acyl-(10-phenylethyl)aziridines initiated the reaction with various acid chlorides to form the corresponding acylaziridinium ion intermediates whose rings were opened by the chloride anion to yield the b-amino-a-chlorocarbonyl compounds. The subsequent displacement of the chloride with the internal oxygen nucleophile originated from methylchloroformate, acetyl chloride, and methyl chlorooxoacetate yielded oxazolidin-2-ones, b-amino-a-acetyloxypropionates, and morpholin-2,3-diones, respectively.

 

 

 

Tetrahedron, 2006, 62, 8844-8849.jpg

 

List of Articles
번호 제목 글쓴이 날짜 조회 수
58 58. Asymmetric formal synthesis of (-)-formoterol and (-)-tamsulosin - Heterocycles - 2007, 2243 imagefile aziridine 2010-05-29 4847
57 57. Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates - Tetrahedron Lett. 2007 48 269-271 imagefile aziridine 2010-05-17 3902
56 56. Selective reduction of C-C double bonds of 2-vinylaziridines:preparation of enantiomerically pure 2-alkylaziridines - Bull. Kor. Chem. Soc. 2009, 3123 imagefile aziridine 2010-05-12 3808
55 55. Dynamic Thermodynamic Resolution:Advantage by Separation of Equilibration and Resolution - Acc. Chem. Res., 2009, 42, 224 imagefile aziridine 2010-05-12 3212
54 54. The preparation of stable aziridinium ions and their ring-openings - Chem. Comm. 2008, 4363–4365 imagefile aziridine 2010-05-12 3803
53 53. Nucleophilic substitution of (sulfonyloxymethyl)aziridines: an asymmetric synthesis of both isomers of mexiletine - Tetrahedron 2008, 64, 11110 imagefile aziridine 2010-05-12 3257
52 52. Sphingosine 1-phosphate (S1P) induces shape change in rat C6 glioma cells through the S1P2 receptor: development of an agonist for S1P receptors - Journal of Pharmacy and Pharmacology 2007, 59, 1035-1041 imagefile aziridine 2010-05-12 3888
51 51. Selective Mono-BOC Protection of diamines - Synth. Comm. 2007, 37, 737-742 imagefile aziridine 2010-05-12 4919
50 50. Bis-styrylpyridine and bis-styrylbenzene derivatives as inhibitors for Aβ fibril formation - Bioorg. Med. Chem. Lett. 2007, 17, 1466-1470 imagefile aziridine 2010-05-12 3162
49 49. Dihydroxylation of 2-vinyl-aziridine: Efficient synthesis of D-ribo-phytosphingosine - Chem. Commun. 2007, 79-81 imagefile aziridine 2010-05-12 3748
» 48. Ring opening of 2-acylaziridines by acid chlorides - Tetrahedron 2006, 62, 8844-8849 imagefile aziridine 2010-05-12 3761
47 47. An efficient synthesis of chiral terminal 1,2-diamines using an enantiomerically pure [1-(10R)-methylbenzyl]aziridine-2-yl]methanol - Tetrahedron 2006, 62, 8393-8397 imagefile aziridine 2010-05-12 3203
46 46. Cyclo(Phe-Pro) Modulates the Expression of ompU in Vibrio spp. - Journal of Bacteriology 2006, 188, 6, 2214 imagefile aziridine 2010-05-12 3811
45 45. Synthesis of constrained ceramide analogs and their potent antileukemic activities - Bioorg. Med. Chem. Lett. 2006, 16, 1880-1883 imagefile aziridine 2010-05-12 4202
44 44. Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles - Tetrahedron. 2005, 9281 imagefile aziridine 2010-05-12 3815
43 43. Synthesis of Functionalized Bicyclic Triazoles from Chiral Aziridines - Synlett. 2005, 14, 2187 imagefile aziridine 2010-05-12 4100
42 42. Lewis acid-catalyzed stereospecific ring expansion of aziridine-2-carboxylates to imidazolidin-2-ones - Chem. Commun. 2005, 24, 3062 imagefile aziridine 2010-05-12 3203
41 41. Preparation of 2,3-diaminopropionate from ring opening of aziridine-2-carboxylate - Tetrahedron Lett. 2005, 46, 4407 imagefile aziridine 2010-05-12 4236
40 40. Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases - Bioorg. Med. Chem. 2005, 13, 3475 imagefile aziridine 2010-05-12 3677
39 39. Stereoselective Addition of Nucleophiles to Aziridinyl-2-carboxaldimine - Bull. Kor. Chem. Soc. 2004, 1617 imagefile aziridine 2010-05-12 3180
38 38. Synthesis and antibacterial activity of arylpiperazinyl oxazolidinones with diversification of the N-substituents - Bioorg. Med. Chem. 2004, 3881 imagefile aziridine 2010-05-12 3484
37 37. Highly Stereoselective Addition of Organomagnesium Reagents to Aziridinyl-2-carboxaldimine: Preparation of Enantiopure 2-Aminomethylaziridines and 4,5-Disubstituted Imidazolidin-2-ones - Synlett. 2004, 489 imagefile aziridine 2010-05-12 3281
36 36. Dicyano{[(1S)-(1-phenylethyl)aziridine-2-yl]methanolato-κ2N,O}boron - Acta Cryst. (2003). C59, 0659-0660 imagefile aziridine 2010-05-12 3214
35 35. Efficient Synthesis of Enantiomerically Pure 2-Acylaziridines - J. Org. Chem. 2003, 68, 7675 imagefile aziridine 2010-05-12 3235
34 34. Hightlights of the Chemistry of Enantiomerically Pure Aziridine-2-Carboxylates - Aldrichimica Acta 2003, 36, 57 imagefile aziridine 2010-05-12 3661
33 33. A Novel Synthesis of 5-Functionalized Oxazolidin-2-ones from Enantiomerically Pure 2-Substituted N-[(R)-(+)-r-Methylbenzyl]aziridines - J. Org. Chem. 2003, 68, 104 imagefile aziridine 2010-05-12 3690
32 32. Novel Stereoselective Synthesis of Functionalized Oxazolidinones from Chiral Aziridines - J. Org. Chem. 2003, 68, 43 imagefile aziridine 2010-05-12 3188
31 31. Facile synthesis of β-anilinopropionates from lewis acid-induced N-methyleneanilines with ketene acetals - Syn. Comm. 2002, 32, 1495 imagefile aziridine 2010-05-12 3089
30 30. An Efficient Synthesis of N-Boc-D-Diphenylalanine from A Chiral Aziridine-2-Carboxylate - Heterocycles 2002, 57, 1143 imagefile aziridine 2010-05-12 3417
29 29. Syntheses of 1b -Methylcarbapenems Bearing 5-Methyl-4-hydroxypyrrolidinone - Chem. Pharm. Bull. 2002, 50, 415 imagefile aziridine 2010-05-12 3125


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