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Substrate Binding in the Asymmetric Dihydroxylation Reaction − Investigation of the Stereoselectivity in the Dihydroxylation of C s ‐Symmetric Divinylcarbinol Derivatives
Author(s) -
Bayer Annette,
Svendsen John S.
Publication year - 2001
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 - 10.1002/1099-0690(200105)2001:9<1769::aid-ejoc1769>3.0.co;2-d
Subject(s) - dihydroxylation , chemistry , osmium tetroxide , stereoselectivity , ligand (biochemistry) , substrate (aquarium) , stereochemistry , allylic rearrangement , osmium , substituent , enantioselective synthesis , organic chemistry , catalysis , ruthenium , biochemistry , electron microscope , physics , receptor , oceanography , geology , optics
The mechanism of the asymmetric dihydroxylation (AD) reaction has been hotly disputed. We have studied the stereochemical outcome of the AD reaction on a series of C s ‐symmetric divinylcarbinol derivatives in order to shed light on the binding mode of the substrate to the osmium tetroxide−ligand complex. The product distribution is dependent on the size of the allylic substituent, and on the type and class of ligand. It is postulated that the diastereospecificity of the reactions originates from attractive forces between the substrate and the ligand. These interactions are independent of the interactions responsible for the enantioselectivity in the AD reaction.