One‐Pot Desymmetrization of  meso ‐1,2‐Hydrocarbon Diols through Acylation and Oxidation | Zendy

Müller Christian E. | Zendy; Zell Daniela | Zendy; Schreiner Peter R. | Zendy

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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.

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