Synthesis of 2-substituted 2-arylmalonates via tricarbonylchromium complexes

Tricarbonylchromium complexes 1 react with monosubstituted malonic acid esters 2 in DMSO at room temperature in the presence of KOtBu to give the complexes 3. After oxidative demetalation, the appropriate aryl derivatives 4 are obtained in moderate to good overall yields. Diastereoselective arylatio...

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Published inJournal für praktische Chemie, Chemiker-Zeitung Vol. 339; no. 3; pp. 261 - 265
Main Authors Deutsch, J, Bartoszek, M, Schneider, M, Zabel, Niclas, HJ
Format Journal Article
LanguageEnglish
Published HEIDELBERG JOHANN AMBROSIUS BARTH VERLAG 01.01.1997
Subjects
Chemistry
Chemistry, Applied
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CARBANIONS
REAGENTS
ARYLATION
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Summary:Tricarbonylchromium complexes 1 react with monosubstituted malonic acid esters 2 in DMSO at room temperature in the presence of KOtBu to give the complexes 3. After oxidative demetalation, the appropriate aryl derivatives 4 are obtained in moderate to good overall yields. Diastereoselective arylations of chirally modified malonates such as 5a-c were studied. The stereoselectivity was highest for the products 6c/6c' (80:20) with (-)-8-phenylmenthol as alcohol component in the malonate 5.
ISSN:0941-1216
DOI:10.1002/prac.19973390146