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Chiral Organometallic Reagents, XI. Stereoselective Exchange of Diastereotopic Iodine Atoms by Magnesium in 3‐Alkoxy‐1,1‐diiodoalkanes
Author(s) -
Hoffmann Reinbard W.,
Kusche Andreas
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270721
Subject(s) - chemistry , stereoselectivity , magnesium , alkoxy group , benzaldehyde , iodide , iodine , reagent , halide , medicinal chemistry , group 2 organometallic chemistry , organic chemistry , stereochemistry , catalysis , molecule , alkyl
α‐Iodoalkylmagnesium species were generated by reaction of 3‐oxygenated 1,1‐diiodoalkanes with isopropylmagnesium halides at −78%C. The resulting magnesium carbenoids were found to be configurationally stable at temperatures up to −20%C and were trapped by benzaldehyde or allyl iodide at low temperatures. Stereoselectivity on exchange of the diastereotopic iodine atoms in 3 was found to be low.