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A simple, efficient, two‐step synthesis of symmetric 2,7‐dialkyl‐1,6‐dioxaspiro[4.4]nonanes
Author(s) -
Ballini Roberto,
Bosica Giovanna,
Uselli Alessandra
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310145
Subject(s) - nitromethane , chemistry , sodium borohydride , michael reaction , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
A two‐step synthesis of symmetric 2,7‐dialkyl‐1,6‐dioxaspiro[4.4]nonanes has been achieved by double Michael addition of nitromethane with two moles of enones on Amberlyst A21, followed by in situ reduction with sodium borohydride, then spontaneous spiroketalization of the obtained nitrodiol, by the Nef reaction under acidic conditions, affords the title compounds in good yields.