THE REGIOCHEMISTRY OF REDUCTION OF MONO-ETHYL FUMARATE AND MALEATE USING A RUTHENIUM BINAP CATALYST

Authors
SHAHARUZZAMAN M BRADDOCKWILKING J CHICKOS JS TAM CN SILVA RAGD KEIDERLING TA
Citation
M. Shaharuzzaman et al., THE REGIOCHEMISTRY OF REDUCTION OF MONO-ETHYL FUMARATE AND MALEATE USING A RUTHENIUM BINAP CATALYST, Tetrahedron : asymmetry, 9(7), 1998, pp. 1111-1114
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
7
Year of publication
1998
Pages
1111 - 1114
Database
ISI
SICI code
0957-4166(1998)9:7<1111:TROROM>2.0.ZU;2-U
Abstract
The regiochemistry of the reduction of mono-ethyl fumarate using iphen ylphosphino)-[R]-1,1-binapthyl}-ruthenium(II) (Ru[BINAP]) in H-2/CH3OD is reported and occurs opposite to the regiochemistry observed in the reduction of tiglic acid. Reduction of mono-ethyl maleate with D-2/CH 3OD is very sluggish but produces meso-dideuteriosuccinic acid with hi gh stereoselectivity. Reduction of mono-ethyl maleate with Ru[BINAP](O 2CR)(2) and H-2/CH3OD results in mono-ethyl succinate-d(1) with nearly complete loss of regiochemistry. (C) 1998 Elsevier Science Ltd. All r ights reserved.