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Transannular [4+3] Cycloadditions of Macrocyclic Epoxy Ketones
Author(s) -
Chan Diana,
Chen Yu,
Low KamHung,
Chiu Pauline
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800019
Subject(s) - epoxy , cycloheptane , cycloaddition , chemistry , yield (engineering) , cycloisomerization , ring (chemistry) , organic chemistry , materials science , catalysis , composite material
Transannular [4+3] cycloadditions of dienophiles derived from macrocyclic epoxy ketones produce fused ring systems having central cycloheptane subunits. In some cases, the base directly induced cycloisomerization of the epoxy ketones to yield the cycloadducts; in others, the epoxy ketones were transformed into their corresponding enolsilanes before undergoing cycloaddition. Enantiomerically enriched tricyclic arrays were obtained from cycloadditions starting from optically pure epoxy ketones.