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Dictating Thermodynamic Control through Tethering: Applications to Stereoselective Bis‐Spiroketal Synthesis
Author(s) -
Asari Austin H.,
Floreancig Paul E.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201916270
Subject(s) - stereoselectivity , stereocenter , degeneracy (biology) , tethering , chemistry , combinatorial chemistry , computational biology , computer science , biology , enantioselective synthesis , bioinformatics , catalysis , biochemistry , operating system
Approaches to stereocontrol that invoke thermodynamic control fail when two or more potential products are energetically similar, but rational structural perturbations can be employed to break the energetic degeneracy and provide selective transformations. This manuscript illustrates that tethering is an effective approach for the stereoselective construction of bis‐spiroketals with thermodynamically similar stereoisomers, providing a new approach to set remote stereocenters and prepare complex structures that have not previously been accessed stereoselectively.