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Enantioselective Synthesis of Arene cis ‐Dihydrodiols from 2‐Pyrones
Author(s) -
Liang XiaoWei,
Zhao Yunlong,
Si XuGe,
Xu MengMeng,
Tan JiaHao,
Zhang ZhiMao,
Zheng ChengGong,
Zheng Chao,
Cai Quan
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201908284
Subject(s) - enantioselective synthesis , chemistry , catalysis , organic chemistry , stereochemistry , combinatorial chemistry
An enantioselective chemical synthesis of arene cis ‐dihydrodiols has been realized from 2‐pyrones through sequential ytterbium‐catalyzed asymmetric inverse‐electron‐demand Diels–Alder (IEDDA) reaction of 2‐pyrones and retro‐Diels–Alder extrusion of CO 2 . By using this strategy, a series of substituted arene cis ‐dihydrodiols can be obtained efficiently with high enantioselectivity (>99 % ee in many cases). Based on this strategy, efficient and concise asymmetric total syntheses of (+)‐MK7607 and 1‐ epi ‐(+)‐MK7607 were accomplished.