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Enantioselective Sulfoxidation and Kinetic Resolution Combined Protocol Mediated by a Functionalized ( S )‐Norcamphor‐Based Hydroperoxide/Titanium( IV ) Isopropoxide System
Author(s) -
Lattanzi Alessandra,
Piccirillo Sandro,
Scettri Arrigo
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600267
Subject(s) - kinetic resolution , chemistry , enantioselective synthesis , yield (engineering) , catalysis , chirality (physics) , titanium , combinatorial chemistry , organic chemistry , thermodynamics , physics , chiral symmetry breaking , quantum mechanics , quark , nambu–jona lasinio model
A functionalized tertiary furyl hydroperoxide derived from ( S )‐norcamphor has been easily synthesized in good yield and in a highly diastereoselective manner. Good to high enantioselectivities (up to 99 % ee ) and acceptable to good yields (up to 86 %) were achieved for the sulfoxides, by tandem stereoconvergent asymmetric sulfoxidation and kinetic resolution when using the novel hydroperoxide as oxygen donor and chirality source in the presence of catalytic loadings of titanium( IV ) isopropoxide as the catalyst.