American Chemical Society
jo9b03302_si_003.cif (702.02 kB)

Catalytic Asymmetric [4 + 2] Cycloaddition of ortho-Alkenyl Naphthols/Phenols with ortho-Quinone Methides: Highly Stereoselective Synthesis of Chiral 2,3,4-Trisubstituted Chromans

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posted on 2020-04-03, 14:17 authored by Shubo Feng, Binmiao Yang, Tao Chen, Ran Wang, Yu-Hua Deng, Zhihui Shao
Chiral phosphoric acid-catalyzed biomimetic asymmetric [4 + 2] cycloaddition of ortho-alkenyl naphthols/phenols and ortho-quinone methides (o-QMs) has been demonstrated to afford various important 2,3,4-trisubstituted chromans in high yields with excellent enantio- and diastereoselectivities (up to 99% yield, 99% ee, >20:1 dr). Notably, this methodology not only enabled access to the trans–cis chiral trisubstituted chromans from 1-alkenyl 2-naphthols but also is compatible with 2-alkenyl 1-naphthols and phenols to deliver trans–trans chiral trisubstituted chromans.