Asymmetric synthesis of (R)- and (S)-4-(substituted benzyl)dihydrofuran-2(3H)-ones: an application of the ruthenium-binap complex-catalysed asymmetric hydrogenation of alkylidenesuccinic acids
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1441-1445
- https://doi.org/10.1039/p19900001441
Abstract
A concise synthesis of (S)- or (R)-4-(substituted benzyl)dihydrofuran-2(3H)-ones (1) with high enantiomeric purity is presented. (S)- or (R)-(Substituted benzyl)succinic acids (6) 97% enantiomeric excess) were first prepared by Ru2Cl4[(R)- or (S)-binap)]2(NEt3) catalysed asymmetric hydrogenation of (substituted benzylidene)succinic acids. The diacids (6) were converted into (R)- or (S)-2-(substituted benzyl)butane-1,4-diols (9), and subsequent RuH2(PPh3)4-catalysed dehydrogenative lactonization of (9) afforded the lactones (1) with complete retention of configuration at the chiral centre.Keywords
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