Synthesis of optically pure vic-sulfanyl amines mediated by a remote sulfinyl group

Organic Letters

Volumn 13, Issue 17, 2011, Pages 4534-4537

  Arroyo, Yolanda ^a   Sanz Tejedor, M Ascensión ^a   Alonso, Inés ^b   García Ruano, José L ^b  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINES; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 80052230974     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201696y     Document Type: Article

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32. relat. = 3.9 kcal/mol) which would explain the absence of this product in the present case. The different behaviour of carbanions with R = Me, in which the C- H•••N bond could have also been formed and R=SMe must be due to the different distribution of the charge, delocalized through the aromatic ring and was stabilized by the sulfinyl group or partially stabilized by the SMe group in the latter case
33. -1), evaluated by means of a second-order perturbational analysis of the Fock matrix, between the lone pair of a nitrogen atom in TS- syn and the C-H antibonding orbital, decreases with the presence of EWG: 2.86, 2.62, and 2.36 from 2a to 2r. The strength of the hydrogen bond C-H•••S in TS- anti also decreases (1.50, 1.25, 1.21, and 1.21 from 2a to 2u). Another very weak C-H•••S bond in TS- syn between the sulfur atom of SMe and the iminic hydrogen could be proposed according to its length (2.81-2.85 Å); however, taking into account the same criteria regarding its strength (less than 0.23) it was considered negligible