Tandem epoxide or aziridine ring opening by azide/copper catalyzed [3+2] cycloaddition: Efficient synthesis of 1,2,3-triazolo β-hydroxy or β-tosylamino functionality motif

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9822-9825

  Kumaraswamy, Gullapalli ^a   Ankamma, Kukkadapu ^a   Pitchaiah, Arigala ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS; EPOXIDATION; STEREOSELECTIVITY;

AZIRIDINE RINGS; PEG-400; SODIUM AZIDE; TANDEM EPOXIDES;

AROMATIC COMPOUNDS;

1,2,3 TRIAZOLE DERIVATIVE; AZIDE; AZIRIDINE; AZIRIDINE DERIVATIVE; COPPER; EPOXIDE; MACROGOL 400; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CYCLOADDITION; STEREOSPECIFICITY; SYNTHESIS;

AZIDES; AZIRIDINES; CATALYSIS; COPPER; CYCLIZATION; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM; TOSYL COMPOUNDS; TRIAZOLES;

EID: 36849051367     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701724f     Document Type: Article

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31. (a) The products (S)-4f, (S)-4g, and (S,S)-4v were converted to the corresponding (S)-MTPA esters. The (S)-MTPA esters of (S)-4f and (S)-4g were analyzed with reference to their respective racemic (S)-MTPA esters on chiral column [Chiral AD-H (220 nm), flow rate = 0.5 mL/min, hexane: 2-propanol (90:10)]. In case of product (S,S)-4v, the ee was estimated by NMR, based on methoxy resonance of (S)-MTPA ester, using the recemic (S)-MTPA ester as reference.
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