Facile Photochemical Synthesis of 1,1?-Binaphthyls
Keyword(s):
The photochemical synthesis of highly functionalized 1,1′-binaphthyls 9 by photodehydro-Diels–Alder reaction of esters 8 is reported. It was found that π-stacking interactions between a naphthyl moiety already present in the reactants 8 and an aryl group tethered in the propargyl position of these esters clearly influence the regio- and diastereoselectivity of the reaction. The formation of undesired phenanthrenes 10 could be suppressed by introduction of a blocking methoxy group in the 2-position of the naphthyl moiety. In one case, a diastereomeric ratio of 32:68 was achieved. This is the first example of an atropselective synthesis of biaryls by a photodehydro-Diels–Alder reaction.
2020 ◽
Keyword(s):
2020 ◽
2020 ◽
2016 ◽
Vol 20
(22)
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pp. 2421-2442
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2014 ◽
Vol 18
(12)
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pp. 1586-1620
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2018 ◽
Vol 15
(2)
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pp. 221-229
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