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Selective Reactions with Organoaluminum Compounds
Author(s) -
Yamamoto Hisashi,
Nozaki Hitosi
Publication year - 1978
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197801691
Subject(s) - allylic rearrangement , reagent , chemistry , organic chemistry , heterolysis , isomerization , terpene , zinc , catalysis
With the aid of selected examples an overview is given of the development trends in highly discriminative reactions using organoaluminum compounds. (1) Isomerization of substituted oxiranes into allyl alcohols has been effected both stereo‐ and regioselectively by means of a new organoaluminum reagent, diethylaluminum 2,2,6,6‐tetramethylpiperidide (DATMP); this reaction which provides a new route for the regiospecific transformation of allyl alcohols into 1,3‐dienes. (2) A novel nonenzymic heterolysis of allylic phosphates of terpenoids has been effected by organoaluminum compounds and has enabled development of a new method for the selective synthesis of cyclic terpenes. (3) The reductive condensation of α‐haloketones with carbonyl compounds in the presence of diethylaluminum chloride and zinc affords β‐hydroxy‐carbonyl derivatives in good yields with exclusion of undesired self‐condensations products.