Journal
ORGANIC LETTERS
Volume 6, Issue 11, Pages 1857-1860Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol049392v
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Lewis-base-catalyzed cycloisomerization of bis(enones) to decalins has been demonstrated as an alternative to the traditional Lewis acid catalyzed Diels-Alder cycloaddition. In this process, a trialkylphosphine mediates both bond formation steps in two distinct catalytic cycles. The single-pot operation generates two carbon-carbon bonds and up to five contiguous stereocenters in one step, starting from achiral, aliphatic substrates; eight examples are provided.
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