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Aluminum Acetals in Organic Synthesis
Author(s) -
Boussonnière Anne,
Bénéteau Romain,
Lebreton Jacques,
Dénès Fabrice
Publication year - 2013
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.201300624
Subject(s) - chemistry , aluminium , reactivity (psychology) , organic synthesis , tetrahedron , ionic bonding , organic chemistry , combinatorial chemistry , computational chemistry , catalysis , ion , medicine , alternative medicine , pathology , crystallography
Aluminum acetals are easily obtained from esters and lactones by reduction with aluminum hydrides. These thermally unstable tetrahedral intermediates have found applications in organic synthesis, with various methodologies taking advantage both of the stabilities of these aluminum species at low temperatures and of their tendencies to undergo rearrangement into the corresponding aldehydes. Efficient one‐pot transformations can be achieved from aluminum acetals under ionic and radical conditions. A comprehensive overview of the reactivity of these species, including the most recent advances in this field, is presented in this microreview.