Sang-Mi Han, Sang-ho Ma, Hyun-Joon Ha, Won Koo Lee                                

      

 The nucleophilic substitution reactions of 1-[1'(R)-a-methylbenzyl]-(2R)-and (2S)-(sulfonyloxymethyl)aziridines were carried out with various nucleophiles including N3-, MeO-, CN-, SCN-, and diarylcuprates. The reaction pathway is influenced by the stereochemistry of the substrates, nucleophiles, and also the structure of the leaving groups. When the reaction site is less sterically hindered for the reactive nucleophiles to approach to the substrate 1-[1'(R)-a-methylbenzyl]-(2S)-(p-toluenesulfonyloxymethyl)aziridines, product is obtained as a single isomer while all the other starting materials afford a mixture of two isomers from two different reaction pathways. Application of this method enabled us to prepare both isomers of orally effective antiarrhythmic agent mexiletine.

 

 

 

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List of Articles
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58 58. Asymmetric formal synthesis of (-)-formoterol and (-)-tamsulosin - Heterocycles - 2007, 2243 imagefile aziridine 2010-05-29 4877
57 57. Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates - Tetrahedron Lett. 2007 48 269-271 imagefile aziridine 2010-05-17 3926
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 3833
55 55. Dynamic Thermodynamic Resolution:Advantage by Separation of Equilibration and Resolution - Acc. Chem. Res., 2009, 42, 224 imagefile aziridine 2010-05-12 3235
54 54. The preparation of stable aziridinium ions and their ring-openings - Chem. Comm. 2008, 4363–4365 imagefile aziridine 2010-05-12 3826
» 53. Nucleophilic substitution of (sulfonyloxymethyl)aziridines: an asymmetric synthesis of both isomers of mexiletine - Tetrahedron 2008, 64, 11110 imagefile aziridine 2010-05-12 3277
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 3907
51 51. Selective Mono-BOC Protection of diamines - Synth. Comm. 2007, 37, 737-742 imagefile aziridine 2010-05-12 4939
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 3184
49 49. Dihydroxylation of 2-vinyl-aziridine: Efficient synthesis of D-ribo-phytosphingosine - Chem. Commun. 2007, 79-81 imagefile aziridine 2010-05-12 3768
48 48. Ring opening of 2-acylaziridines by acid chlorides - Tetrahedron 2006, 62, 8844-8849 imagefile aziridine 2010-05-12 3787
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 3226
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 3828
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 4220
44 44. Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles - Tetrahedron. 2005, 9281 imagefile aziridine 2010-05-12 3830
43 43. Synthesis of Functionalized Bicyclic Triazoles from Chiral Aziridines - Synlett. 2005, 14, 2187 imagefile aziridine 2010-05-12 4122
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 3220
41 41. Preparation of 2,3-diaminopropionate from ring opening of aziridine-2-carboxylate - Tetrahedron Lett. 2005, 46, 4407 imagefile aziridine 2010-05-12 4257
40 40. Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases - Bioorg. Med. Chem. 2005, 13, 3475 imagefile aziridine 2010-05-12 3695
39 39. Stereoselective Addition of Nucleophiles to Aziridinyl-2-carboxaldimine - Bull. Kor. Chem. Soc. 2004, 1617 imagefile aziridine 2010-05-12 3289
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 3499
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 3302
36 36. Dicyano{[(1S)-(1-phenylethyl)aziridine-2-yl]methanolato-κ2N,O}boron - Acta Cryst. (2003). C59, 0659-0660 imagefile aziridine 2010-05-12 3240
35 35. Efficient Synthesis of Enantiomerically Pure 2-Acylaziridines - J. Org. Chem. 2003, 68, 7675 imagefile aziridine 2010-05-12 3259
34 34. Hightlights of the Chemistry of Enantiomerically Pure Aziridine-2-Carboxylates - Aldrichimica Acta 2003, 36, 57 imagefile aziridine 2010-05-12 3677
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 3708
32 32. Novel Stereoselective Synthesis of Functionalized Oxazolidinones from Chiral Aziridines - J. Org. Chem. 2003, 68, 43 imagefile aziridine 2010-05-12 3201
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 3104
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 3441
29 29. Syntheses of 1b -Methylcarbapenems Bearing 5-Methyl-4-hydroxypyrrolidinone - Chem. Pharm. Bull. 2002, 50, 415 imagefile aziridine 2010-05-12 3146


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