Jae Hyun Bae, Seong-Ho Shin, Chan Sun Park, and Won Koo Lee                            

 

 

Various enantiomerically pure aziridine-2-methanol derivatives were reacted with thiophenol in methylene chloride at room temperature to obtain ring-opening products in high yields with excellent regioselectivity. The reaction procedure is very simple and it provides highly functionalized chiral molecules potentially useful for the synthesis of many biologically important compounds. The reaction rate was found to increase with the acidity of thiols.

 

 

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List of Articles
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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 3303
27 27. Synthesis of Substituted-(l)-Tryptophanols from an Enantiomerically Pure Aziridine-2-methanol - Org. Lett. 2001, 3, 4197. imagefile aziridine 2010-05-12 3457
26 26. New Uses of Amino Acids as Chiral Building Blocks in Organic Synthesis - Org. Lett. 2001, 3, 3119 imagefile aziridine 2010-05-12 3437
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 4098
24 24. New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates - Tetrahedron 2001, 57, 9655 imagefile aziridine 2010-05-12 4069
23 23. Synthesis of Quaternary Ammoniocephalosporin Having Two Vinyl Groups Using Radical Promoted Thermal Isomerization - Bull. Kor. Chem. Soc. 2001, 22, 659 imagefile aziridine 2010-05-12 3420
22 22. Selective production of difluoromethyl methyl ether from chlorodifluoromethane using alkali metal carbonates - J. Fluorine Chem. 2001, 107, 133 imagefile aziridine 2010-05-12 4314
21 21. Cycloaddition of Lewis Acid-Induced N-Methyleneanilines as Azadienes to 1,2-Bistrimethylsilyloxycyclobutene and Oxidative Ring Expansion to 1,2,4,5-Tetrahydro-1-benzazocine-3,6-diones - J. Org. Chem. 2000, 65, 8384 imagefile aziridine 2010-05-12 3419
20 20. Stereoselective synthesis of enantiomerically pure D-threo-PDMP; manipulation of a core 2,3-diamino alcohol unit - Tetrahedron : Asymmetry 2000, 11, 3283 imagefile aziridine 2010-05-12 3335
19 19. Stereoselective synthesis of protected threo-β-hydroxy-L-glutamic acid using a chiral aziridine - Tetrahedron : Asymmetry 2000, 11, 3283 imagefile aziridine 2010-05-12 3698
» 18. Preparation of Cysteinol Derivatives by Highly Regioselective Ring Opening Nonactivated Chiral Aziridines by Thiols - Tetrahedron 1999, 55, 10041 imagefile aziridine 2010-05-12 3511
17 17. The Thiazole Route to 2-Formyl-1β-Methylcarbapenem - Bull. Kor. Chem. Soc. 1998, 19, 1294 imagefile aziridine 2010-05-12 3144
16 16. Synthesis of Substituted (D)-Phenylalanine Derivatives by Regioselective Reduction of Enantiomerically Pure cis-2,3-Disubstituted Aziridines - Tetrahedron Lett. 1998, 39, 9193 imagefile aziridine 2010-05-12 3394
15 15. Preparation of both (D)- and (L)-serinol derivatives from N-[(S)-a-methylbenzyl]-aziridine-2(S)-methanol - Heterocycles 1998, 48, 1917 imagefile aziridine 2010-05-12 3170
14 14. A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor - Tetrahedron : Asymmetry 1998, 9, 983 imagefile aziridine 2010-05-12 2959
13 13. Efficient Syntheses of (1R,2R)- and (1S,2S)-2-Amino-1-alkyl(oraryl)-1,3-propanediols by Regioselective Ring Opening of Aziridine-2-methanols - J. Org. Chem. .1997, 743 imagefile aziridine 2010-05-12 3435
12 12. Highly diastereoselective reduction of enantiomerically pure aziridino ketones - Tetrahedron 1996, 52, 12117 imagefile aziridine 2010-05-06 3147
11 11. An Effcient synthesis of both enantiomers of cathinone by regioselective reductive ring opening of substituted aziridines - Tetrahedron 1996, 52, 12111 imagefile aziridine 2010-05-06 3167
10 10. Efficient Synthesis of Ephedra Alkaloid Analogues Using an Enantiomerically Pure N-[(R)-(+)-r-Methylbenzyl]aziridine-2-carboxaldehyde - J. Org. Chem. 1996, 61, 6183 imagefile aziridine 2010-05-06 3260
9 9. Resiospecific reductive ring cleavage of N-substituted aziridine-2-carboxylates and an aziridine-2-methanol via catalytic hydrogenation using Pd as a catalyst - Tetrahedron Lett. 1995, 36, 8431 imagefile aziridine 2010-05-06 3135
8 8. Chirospecific Syntheses of Precursors of Cyclopentane and cyclopentene Carbocyclic Nucleosides by [3 + 33-Coupling and Transannular Alkylation - J. Org. Chem. 1995, 60, 4602 imagefile aziridine 2010-05-06 3252
7 7. Regioselective N-Methyl Carbon Lithiation of N-Boc-MethylalkylaminrylamiEnxepae dient Synthesis of Unsymmetrical Amines - Tetrahedron Lett. 1994, 35, 4067 imagefile aziridine 2010-05-06 3111
6 6. Chirospecific Synthesis of (1S,3R)-l-Amino-3-(hydroxymethyl)cyclopentane a Precursor for Carbocyclic Nucleoside Synthesis. Intramolecular Aziridine Cyclizations - J. Org. Chem. 1993, 58, 5019 imagefile aziridine 2010-05-06 3005
5 5. a-Lithioamine Synthetic Equivalents: Syntheses of Diastereoisomers from Boc Derivatives of Cyclic Amines - J. Org. Chem. 1993, 58, 1109 imagefile aziridine 2010-05-06 2973
4 4. Endocyclic Restriction Test: Evaluation of Transition-Structure Geometry for an Aryl Bromide-Alkyllithium Exchange Reaction - J. Am. Chem. Soc. 1990, 112, 1629 imagefile aziridine 2010-05-06 2899
3 3. a-Lithioamine Synthetic Equivalents: Syntheses of Diastereoisomers from the Boc Piperidines - J. Org. Chem. 1990, 55, 2578 imagefile aziridine 2010-05-06 2815
2 2. a-Lithioamine synthetic equivalents from dipole-stabilized carbaniones: The r-Boc group as an activator for a’-Lithiation of carbamates - Tetrahedron Lett. 1989, 30, 1197 imagefile aziridine 2010-05-06 2299
1 1. Regiospecific Alkylation of Allylic Halides with Latent-γ-Functionality - J. Org. Chem. 1984, 49, 1838 imagefile aziridine 2010-05-06 2306


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