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One‐Pot Desymmetrization of meso ‐1,2‐Hydrocarbon Diols through Acylation and Oxidation
Author(s) -
Müller Christian E.,
Zell Daniela,
Schreiner Peter R.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901711
Subject(s) - desymmetrization , racemization , acylation , chemistry , enantiomer , yield (engineering) , enantiomeric excess , nucleophile , organic chemistry , catalysis , enantioselective synthesis , materials science , metallurgy
Avoid racemization! Short lipophilic oligopeptides utilizing nucleophilic N ‐π‐methyl histidine residues catalyze the desymmetrization of meso ‐1,2‐diols with enantiomeric ratios of up to 94:6. Direct one‐pot oxidation, which avoids the well‐known racemization of the monoacylated product, directly leads to α‐acetoxy ketones with enantiomeric ratios of up to 97:3 and 97 % yield.