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Diastereoselective Deprotonative Metalation of Sugar‐Derived Ferrocene Esters Using Mixed Lithium–Cadmium Combinations
Author(s) -
Sreeshailam Aare,
Dayaker Gandrath,
Chevallier Floris,
Roisnel Thierry,
Krishna Palakodety Radha,
Mongin Florence
Publication year - 2011
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.201100264
Subject(s) - chemistry , metalation , lithium (medication) , ferrocene , yield (engineering) , amide , cadmium , sugar , organic chemistry , medicinal chemistry , electrochemistry , materials science , electrode , metallurgy , endocrinology , medicine
The ability of a mixed lithium–cadmium amide to deproto‐metallate diastereoselectively several sugar‐derived ferrocene esters was studied. The ferrocenecarboxylates generated from α‐ D ‐glucofuranoses gave the best results, as evidenced after subsequent trapping with iodine. Good chemical yields and diastereoselectivities up to 82 % in favor of the S P stereoisomer were obtained. The use of a different chiral group favored the formation of the R P stereoisomer, isolated in 34 % yield and 98 % diastereoselectivity.
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