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Modular Construction of Topologically Complex Polycyclic Acetals by Tether‐Controlled Domino Reactions
Author(s) -
Castillo Rafael R.,
Abet Valentina,
Aquino Maurizio,
Gandara Zoila,
Retailleau Pascal,
Arseniyadis Siméon
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201481
Subject(s) - stereocenter , regioselectivity , chemistry , domino , methylene , stereochemistry , cascade reaction , ring (chemistry) , oxidative cleavage , axial chirality , modular design , chirality (physics) , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry , enantioselective synthesis , chiral symmetry breaking , physics , quantum mechanics , quark , computer science , nambu–jona lasinio model , operating system
Lead tetraacetate mediated oxidative cleavage of octalin‐diols ( 1 and 1′ ), tethered by variously substituted arenes placed at the angular position (C11), show switchable regioselectivity effects. A highly selective set of regiochemical outcomes can be achieved, producing a range of polycyclic acetals through competing domino paths (A–E). The modular complexity inherent in the type‐ 1 domino precursors is derived from the C11 configuration, where the course of ring‐forming processes is controlled from the chirality at a remote stereocenter (C11). For methylene‐tethered type‐ 1′ precursors, the regiochemical outcome is mainly determined by controlling the reaction parameters.