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Asymmetric Catalytic [3+2] Annulation of Donor‐Acceptor Cyclopropane with Cyclic Ketones: Facile Access to Enantioenriched 1‐Oxaspiro [4.5]decanes †
Author(s) -
Zheng ZhongBo,
Cheng WenFu,
Wang Lijia,
Zhu Jun,
Sun XiuLi,
Tang Yong
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000277
Subject(s) - chemistry , annulation , enantioselective synthesis , cyclopropane , yield (engineering) , catalysis , combinatorial chemistry , acceptor , stereochemistry , organic chemistry , ring (chemistry) , materials science , physics , metallurgy , condensed matter physics
Summary of main observation and conclusion A copper catalyzed enantioselective [3+2] annulation of donor‐acceptor cyclopropanes with cyclic ketones has been developed, providing a concise protocol to enantioenriched 1‐oxaspiro[4.5]decanes in up to 98% yield with up to >99/1 dr and up to 92% ee. In addition, this method also provides a facile access to the enantioselective desymmetrisation of various 4‐substituted cyclohexanones. The resulting products were easily converted to the core structures of two natural products Heliespirones A and halogenated sesquiterpene isolated from L . saitoi.
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