Heck reaction hydrindans

The enormous potential of the intramolecular Heck reactions has been demonstrated impressively in elegant syntheses of even the most complicated natural product skeletons. The intramolecular Heck reaction on the achiral iodoalkenes 354 and the corresponding alkenyl triflates 357 with their pairs of enantiotopic double bonds in the cyclohexa-1,4-diene moieties, applying catalysts with chiral ligands, gave tetrahydronaphthalenes 359 or hydrindanes from precursors such as 354, 357 or corresponding precursors with one less carbon in the tether [204f], with excellent enantioselectivities. Complementary to the asymmetrically induced inter-molecular arylation with triflates (Scheme 8.72), reasonable asymmetric inductions in intramolecular reactions were also achieved with iodides on the addition of silver salts to promote the formation of cationic intermediates such as 356 (Scheme 8.73)... 

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