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Sulfone Group as a Versatile and Removable Directing Group for Asymmetric Transfer Hydrogenation of Ketones
Author(s) -
Vyas Vijyesh K.,
Clarkson Guy J.,
Wills Martin
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004658
Subject(s) - sulfone , transfer hydrogenation , group (periodic table) , chemistry , enantioselective synthesis , ring (chemistry) , functional group , transfer (computing) , reduction (mathematics) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , polymer , computer science , ruthenium , mathematics , geometry , parallel computing
The sulfone functional group has a strong capacity to direct the asymmetric transfer hydrogenation (ATH) of ketones in the presence of [(arene)Ru(TsDPEN)H] complexes by adopting a position distal to the η 6 ‐arene ring. This preference provides a means for the prediction of the sense of asymmetric reduction. The sulfone group also facilitates the formation of a range of reduction substrates, and its ready removal provides a route to enantiomerically enriched alcohols that would otherwise be extremely difficult to prepare by direct ATH of the corresponding ketones.