Publication

글 수 73

72. Chiral aziridine-2-carboxylates: versatile precursors for functionalized tetrahydroisoquinoline (THIQ) containing heterocycles, Tetrahedron 68 (2012) 883-893

조회 수 52 추천 수 0 2012.01.27 21:56:03
aziridine *.239.207.96

  Kyu Myung Lee, Jong Chan Kim, Philjun Kang, Won Koo Lee*, Heesung Eum, Hyun-Joon Ha*


 

Preparation of functionalized 3,4-dihydroisoquinolines 17aej from (S)-N-methoxy-N-methyl-1-[(R)-
1-phenylethyl]aziridine-2-carboxamide 4 is an effective route for the synthesis of 3-(hydroxymethyl)-
1,2,3,4-tetrahydroisoquinolin-4-ols. Stereoselective reduction of the cyclic imines 17aej resulted
in (1S,3S,4R)-4-(tert-butyldimethylsilyl-oxy)-3-[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2-
disubstituted-1,2,3,4-tetrahydroisoquinolines and the desilylation of the TBS groups afforded (1S,3S,4R)-
3-(hydroxymethyl)-6,7-dimethoxy-1,2-disubstituted-1,2,3,4-tetrahydroisoquinolin-4-ols 19aei in good
yields. Also, an asymmetric synthesis of novel tetracyclic 3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinolin-
4-ols 23 and 25 was successfully achieved via Pd-catalyzed N-arylation and CeC coupling reaction.

 

 

2.png3.png

이 게시물을...
첨부
엮인글 :
http://aziridine.cafe24.com/2628/eec/trackback
목록
List of Articles
번호 제목 글쓴이 날짜 조회 수
73 73. Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines, Org. Biomol. Chem., 2011, 9, 1372 imagefile aziridine 2012-01-27 58
» 72. Chiral aziridine-2-carboxylates: versatile precursors for functionalized tetrahydroisoquinoline (THIQ) containing heterocycles, Tetrahedron 68 (2012) 883-893 imagefile aziridine 2012-01-27 52
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 52
70 70. N-Methylative aziridine ring opening and asymmetric synthesis of MeBmt. Tetrahedron Letters 52 (2011) 5918–5920 imagefile aziridine 2012-01-27 52
69 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 50
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 1004
67 67. Aminostyrylbenzofuran derivatives as potent inhibitors for Aβ fibril formation-BMCL, 2008, 18, 5591-5593 imagefile aziridine 2010-09-27 1364
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 1460
65 65. A formal synthesis of (-)-swainsonine from a chiral aziridine - Tetrahedron Lett. 2010, 51, 3284 imagefile aziridine 2010-05-29 1552
64 64. Conjugate addition of amines to chiral 3-aziridin-2-yl-acrylates - Tetrahedron Lett. 2010, 2181 imagefile aziridine 2010-05-29 1549
63 63. Synthesis of substituted imidazolidin-2-ones as aminoacyl-tRNA synthase inhibitors - Bull.Kor.Chem.Soc. 2010, 611 imagefile aziridine 2010-05-29 1469
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 1315
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 1277
60 60. Synthesis of D-erythro-sphingosine from D-ribo-phytosphingoshine - Bull. Kor. Chem. Soc. 2009, 535 imagefile aziridine 2010-05-29 1208
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 1263
58 58. Asymmetric formal synthesis of (-)-formoterol and (-)-tamsulosin - Heterocycles - 2007, 2243 imagefile aziridine 2010-05-29 1666
57 57. Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates - Tetrahedron Lett. 2007 48 269-271 imagefile aziridine 2010-05-17 1249
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 1171
55 55. Dynamic Thermodynamic Resolution:Advantage by Separation of Equilibration and Resolution - Acc. Chem. Res., 2009, 42, 224 imagefile aziridine 2010-05-12 994
54 54. The preparation of stable aziridinium ions and their ring-openings - Chem. Comm. 2008, 4363–4365 imagefile aziridine 2010-05-12 1201
53 53. Nucleophilic substitution of (sulfonyloxymethyl)aziridines: an asymmetric synthesis of both isomers of mexiletine - Tetrahedron 2008, 64, 11110 imagefile aziridine 2010-05-12 1020
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 1176
51 51. Selective Mono-BOC Protection of diamines - Synth. Comm. 2007, 37, 737-742 imagefile aziridine 2010-05-12 1644
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 1118
49 49. Dihydroxylation of 2-vinyl-aziridine: Efficient synthesis of D-ribo-phytosphingosine - Chem. Commun. 2007, 79-81 imagefile aziridine 2010-05-12 1114
48 48. Ring opening of 2-acylaziridines by acid chlorides - Tetrahedron 2006, 62, 8844-8849 imagefile aziridine 2010-05-12 1116
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 1119
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 1269
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 1493
44 44. Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles - Tetrahedron. 2005, 9281 imagefile aziridine 2010-05-12 1215
43 43. Synthesis of Functionalized Bicyclic Triazoles from Chiral Aziridines - Synlett. 2005, 14, 2187 imagefile aziridine 2010-05-12 1075
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 1075
41 41. Preparation of 2,3-diaminopropionate from ring opening of aziridine-2-carboxylate - Tetrahedron Lett. 2005, 46, 4407 imagefile aziridine 2010-05-12 1449
40 40. Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases - Bioorg. Med. Chem. 2005, 13, 3475 imagefile aziridine 2010-05-12 1153
39 39. Stereoselective Addition of Nucleophiles to Aziridinyl-2-carboxaldimine - Bull. Kor. Chem. Soc. 2004, 1617 imagefile aziridine 2010-05-12 1073
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 1077
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 1054
36 36. Dicyano{[(1S)-(1-phenylethyl)aziridine-2-yl]methanolato-κ2N,O}boron - Acta Cryst. (2003). C59, 0659-0660 imagefile aziridine 2010-05-12 1056
35 35. Efficient Synthesis of Enantiomerically Pure 2-Acylaziridines - J. Org. Chem. 2003, 68, 7675 imagefile aziridine 2010-05-12 1087
34 34. Hightlights of the Chemistry of Enantiomerically Pure Aziridine-2-Carboxylates - Aldrichimica Acta 2003, 36, 57 imagefile aziridine 2010-05-12 1075
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 1105
32 32. Novel Stereoselective Synthesis of Functionalized Oxazolidinones from Chiral Aziridines - J. Org. Chem. 2003, 68, 43 imagefile aziridine 2010-05-12 1048
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 1150
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 1157
29 29. Syntheses of 1b -Methylcarbapenems Bearing 5-Methyl-4-hydroxypyrrolidinone - Chem. Pharm. Bull. 2002, 50, 415 imagefile aziridine 2010-05-12 1117
28 28. Synthesis and SAR of Aziridinylquinoline-5,8-diones as Agents against Malignant Tumor Cells - Bull. Kor. Chem. Soc. 2001, 22, 1067 imagefile aziridine 2010-05-12 1093
27 27. Synthesis of Substituted-(l)-Tryptophanols from an Enantiomerically Pure Aziridine-2-methanol - Org. Lett. 2001, 3, 4197. imagefile aziridine 2010-05-12 1058
26 26. New Uses of Amino Acids as Chiral Building Blocks in Organic Synthesis - Org. Lett. 2001, 3, 3119 imagefile aziridine 2010-05-12 1030
25 25. Asymmetric synthesis of β-amino-α-hydroxy acids through Lewis acid-mediated addition of ketone acetal to imines - Bull. Chem. Soc. Jpn. 2001, 74, 1667 imagefile aziridine 2010-05-12 1546
24 24. New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates - Tetrahedron 2001, 57, 9655 imagefile aziridine 2010-05-12 1414
목록
쓰기
XE Login