Bulletin of the Chemical Society of Japan p. 3301 - 3307 (1980)
Update date:2022-08-30
Topics:
Maruoka, Keiji
Hashimoto, Shinsuke
Kitagawa, Yoshizo
Yamamoto, Hisashi
Nozaki, Hitosi
A new approach has been demonstrated for the regiospecific aldol synthesis by the simultaneous addition of α-halo carbonyl derivatives and aldehydes or ketones to a suspension of diethylaluminium chloride and zinc in tetrahydrofuran at low temperature.This technique is also employable under mild conditions for the Reformatsky reaction to give β-hydroxy esters in excellent yield.One of the unique synthetic applications of this process is illustrated by the intramolecular cyclization of α-bromo esters of ω-hydroxy aldehyde,which produces macrolides, an important cla ss of compounds in the antibiotic field.
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