Stereoselective control of planar α-dimethylsulfonium benzyl carbanions. Synthesis of optically pure trans-aziridines

Journal of Organic Chemistry

Volumn 74, Issue 11, 2009, Pages 4217-4224

  Arroyo, Yolanda ^a   Meana, Ángela ^a   Rodríguez, J Félix ^a   Sanz Tejedor, M Ascensión ^a   Alonso, Inés ^b   Ruano, José L García ^b  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINES; CHEMICAL EQUATIONS; DIASTEREO-SELECTIVITY; RELATIVE STABILITIES; STEREOSELECTIVE CONTROL; SULFONIUM SALTS; SULFUR ATOMS; THEORETICAL CALCULATIONS; TRANS-SELECTIVITY; TRANSITION STATE;

CHEMICAL REACTIONS;

SULFUR;

ALPHA DIMETHYLSULFONIUM BENZYL CARBANION; AZIRIDINE DERIVATIVE; CARBANION; DIMETHYL [2 (4 TOLUENESULFINYL)PHENYL]SULFONIUM SALT; LITHIUM; N SULFINYLIMINE; REAGENT; SULFUR; UNCLASSIFIED DRUG; YLIDE;

ARTICLE; AZIRIDINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; ISOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ANIONS; AZIRIDINES; IMINES; STEREOISOMERISM;

EID: 66249113529     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900381b     Document Type: Article

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63. +, the more favored the planar free carbanion conformation.
64. -1 less stable than the corresponding cisoid one (TS1b). Probably the transoid approach in our case is destabilized due to steric interactions with the ortho TolSO group in the ylide.
65. The optimization of this type of transition states has not been still possible due to the high degree of conformational freedom shown by all the ligands around the metal. It is being tried with a simple substrate.