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Synthesis and Structural Characterization of Planar Chiral Cr(CO) 3 ‐Complexed Aromatic Nitrones – Valuable Substrates for Asymmetric SmI 2 ‐Induced Coupling Reactions
Author(s) -
ChavarotKerlidou Murielle,
Rivard Michaël,
Chamiot Bénédicte,
Hahn Franck,
RoseMunch Françoise,
Rose Eric,
Py Sandrine,
Herson Patrick
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900836
Subject(s) - chemistry , reactivity (psychology) , nitrone , cyclic voltammetry , intramolecular force , pinacol , coupling reaction , aryl , stereochemistry , aromaticity , enantioselective synthesis , medicinal chemistry , molecule , organic chemistry , cycloaddition , catalysis , electrochemistry , medicine , alternative medicine , electrode , pathology , alkyl
The synthesis of Cr(CO) 3 ‐complexed aromatic nitrones 2 is reported. These new planar‐chiral complexes were fully characterized in solution by 1 H and 13 C NMR, IR and cyclic voltammetry. Moreover, structural data were obtained from X‐ray structures of nitrones 2b , 2d , 2e and 2f . These analyses converge to give evidence of a favoured anti conformation of ortho ‐substituted nitrones, with an unusual N–O ··· H aryl intramolecular interaction forming a six‐membered ring. The reactivity of these chiral nitrones in SmI 2 ‐induced pinacol‐type reactions was investigated. The reductive cross‐coupling of nitrones 2a – d with carbonyl compounds proved to be highly chemo‐ and diastereoselective and afforded precursors of enantioenriched β‐amino alcohols in excellent yields.