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Radical Cyclization of α ‐Bromo Aluminum Acetals: An Easy Approach to γ ‐Lactols
Author(s) -
Boussonnière Anne,
Dénès Fabrice,
Lebreton Jacques
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200905167
Subject(s) - aluminium , chemistry , reaction conditions , medicinal chemistry , organic chemistry , catalysis
Running rings around aluminum : An efficient procedure for radical cyclization of α ‐bromo esters is reported. Reduction of the esters by DIBAL‐H at low temperature gives aluminum acetals, which are cyclized in the presence of n Bu 3 SnH and Et 3 B (see scheme). These one‐pot conditions lead to polysubstituted γ ‐lactols in high yields, and the mildness of the reaction conditions allows the preparation of acid‐sensitive derivatives.