Catalytic Site-, Diastereo-, and Enantioselective Cascade Iodocyclization of 2-Geranylarenols
Yasutaka Tsuji1, Kazumasa Kon1,2, Takahiro Horibe1
1Graduate School of Engineering, Nagoya University, B2-3(611), Furo-cho, Chikusa, Nagoya, 464-8603, Japan.
Abstract:
A chiral amidophosphate-N-iodosuccinimide cooperative catalysis has been developed for the site-, diastereo-, and enantioselective iodocyclization of 2-geranylarenols with molecular iodine to give the corresponding iodo-containing polycyclic compounds with good levels of selectivity. This is the first example of a catalytic enantioselective iodocarbocyclization. A reactive chiral iodonium species is generated from molecular iodine via the dual halogen-bonding interactions with a chiral Lewis base and Lewis acid. The sterically demanding 3,3'-substituents of the chiral BINOL-derived amidophosphate are critical to induce the site-selective iodination at the less-hindered terminal alkenyl moiety of 2-geranylarenols.
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