1,2:5,6‐Di‐ O ‐isopropylidene‐α‐D‐gulofuranose as a Chiral Auxiliary in the Diastereoselective  C  Methylation of Ester Enolates. The Influence of the Base on the Stereochemistry of Enolate Formation and Alkylation | Zendy

Mulzer Johann | Zendy; Hiersemann Martin | Zendy; Buschmann Jürgen | Zendy; Luger Peter | Zendy

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1,2:5,6‐Di‐ O ‐isopropylidene‐α‐D‐gulofuranose as a Chiral Auxiliary in the Diastereoselective C Methylation of Ester Enolates. The Influence of the Base on the Stereochemistry of Enolate Formation and Alkylation

Author(s) -

Mulzer Johann,

Hiersemann Martin,

Buschmann Jürgen,

Luger Peter

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960502

Subject(s) - chemistry , lithium (medication) , base (topology) , methylation , keto–enol tautomerism , amide , lithium amide , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , tautomer , biochemistry , catalysis , gene , medicine , mathematical analysis , mathematics , endocrinology

The C methylation of the carbohydrate‐derived O ‐chiral esters 5a‐d to derivatives 8 proceeds with ( R ) selection of 1:1 to 10:1 and depends primarily on the base used for enolate generation. Lithium 2,2,6,6‐tetramethylpiperide (LTMP) shows the highest and lithium hexamethyldisilazanide (LHMDS) the lowest selection. These results are interpreted in terms of a “post‐enolization complex” involving the lithium amide base.

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