Table 2. Selective 4π and 6π Electrocyclizations of Dienyl Diketones 1a.
Reaction conditions: nucleophile (1 equiv) was added to substrate in THF (1 M), and the reaction was monitored by TLC or NMR.
Product is formed by Nazarov cyclization followed by DABCO elimination.
Twenty percent of 2H-pyran product 3g was also observed.
Product obtained as an inseparable mixture of diastereoisomers: 1.2:1 dr (2g) and 6:1 dr (2h) as determined by 1H NMR spectroscopy.