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Synthesis of Unfunctionalized Carbonated Fragments Containing Two Vicinal Chiral Centers: Stereocontrolled Benzylation of Vinylsulfones Mediated by a Remote Sulfinyl Group
Author(s) -
García Ruano José Luis,
Schöpping Christine,
Alvarado Cuauhtémoc,
Alemán José
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001006
Subject(s) - carbanion , stereoselectivity , vicinal , chemistry , group (periodic table) , optically active , scheme (mathematics) , stereochemistry , combinatorial chemistry , organic chemistry , mathematics , catalysis , mathematical analysis
One‐pot benzylation of ( E )‐vinylsulfones with optically pure 2‐ p ‐tolylsulfinylbenzyl carbanions and desulfinylation with t BuLi, followed by desulfonylation of the resulting 1‐sulfonylpropanes, provided acyclic hydrocarbons containing two connected chiral centers in very smooth conditions and almost complete control of the stereoselectivity (see scheme).