Pyrrolo[2,1-b]thiazole derivatives by asymmetric 1,3-dipolar reactions of thiazolium azomethine ylides to activated vinyl sulfoxides

Journal of Organic Chemistry

Volumn 73, Issue 21, 2008, Pages 8484-8490

  Ruano, José Luis García ^a   Fraile, Alberto ^a   Martín, M Rosario ^a   González, Gema ^a   Fajardo, Cristina ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; KETONES; SULFUR COMPOUNDS;

ALKOXY GROUPS; AZOMETHINE YLIDES; CHEMICAL EQUATIONS; DOUBLE BONDS; ENANTIOPURE; FACIAL SELECTIVITIES; STEREOSELECTIVE MANNERS; SULFINYL GROUPS; THIAZOLE DERIVATIVES; VINYL SULFOXIDES;

INFRARED SPECTROGRAPHS;

3 (4 TOLYL)SULFINYLACRYLONITRILE; AZOMETHINE YLIDE; FURANONE DERIVATIVE; NITRILE; PYRROLO[2,1 B]THIAZOLE DERIVATIVE; SULFINYLFURANONE DERIVATIVE; SULFOXIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYL SULFOXIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

AZO COMPOUNDS; SULFOXIDES; THIAZOLES; THIOSEMICARBAZONES; VINYL COMPOUNDS;

EID: 55249126830     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801705d     Document Type: Article

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41. Nevertheless, the electrostatic repulsion between the sulfinyl and carbonyl oxygens suggests for 6a and 6b that rotamers B must be the most stable ones (it has been supported by theoretical calculations in compounds of similar structure). The reason justifying that the more reactive conformation with ylides is A (with the p-tolyl group in ami relationship with respect to the carbonyl oxygen) can be the electrostatic repulsion between the sulfinyl oxygen and the negative end of the dipole, which would be larger when the latter attacks to the dipolarophile at its conformation B.