RSC Advances p. 63445 - 63462 (2016)
Update date:2022-08-11
Topics:
Kalmode, Hanuman P.
Maity, Dilip K.
Bhate, Prakash M.
The intramolecular Diels-Alder (IMDA) reaction of furanose tethered 1,3,9-decatrienes (4a-4r) was investigated under thermal conditions and in the presence of a Lewis acid. The stereoselectivity was determined by establishing the structures of adducts through single crystal X-ray diffraction and 1H NMR spectroscopy. It was found that contrary to expectations, the thermal IMDA reaction of (3E) and (3Z)-1,3,9-decatrienes proceeded with nearly equal rate and furnished IMDA adducts (6-25) with moderate stereoselectivity. In some cases, rearranged products (9, 12, 17 and 24) arising out of a 1,5-sigmatropic shift, cis-trans isomerization followed by IMDA reaction were formed. In contrast, a Lewis acid promoted IMDA reaction afforded only one adduct albeit in lower yields. Not surprisingly, cis-boat transition states were favored over trans-boat transition states. Experimental results were corroborated with transition state modeling of these reactions by applying density functional theory based electronic structure calculations.
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