- An Asymmetric Synthesis of 2,4-Dimethylvalerolactone and Mevalonolactone using Chiral Binaphthyldiamine Derivatives
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Axially dissymmetric binaphthyldiamine derivatives formed by asymmetric ring opening of the cyclic anhydrides (3) and (4) ring close on hydrolysis to give (-)-cis-2,4-dimethylvalerolactone (6) and (-)-mevalonolactone (7) in 92percent and 58percent enantiomeric excess (e.e.), respectively; similarly the derivative of the racemic cyclic anhydride (+/-)-(3) ring closes to give (-)-trans-2,4-dimethylvalerolactone with 74percent e.e.
- Kawakami, Yukio,Hiratake, Jun,Yamamoto, Yukio,Oda, Jun'ichi
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- All-catalytic, efficient, and asymmetric synthesis of α,ω- diheterofunctional reduced polypropionates via "one-pot" Zr-catalyzed asymmetric carboalumination - Pd-catalyzed cross-coupling tandem process
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A highly efficient method for the synthesis of stereochemically pure (≥99% ee and >50/1 dr) α,ω-diheterofunctional reduced polypropionates has been developed. The essential features of the method are represented by the conversion of inexpensive styrene in
- Novak, Tibor,Tan, Ze,Liang, Bo,Negishi, Ei-Ichi
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p. 2838 - 2839
(2007/10/03)
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- Enzymes in Organic Synthesis, 19. The Enzyme-Catalyzed Sequential Esterification of (+/-)-anti-2,4-Dimethylglutaric Anhydride. - An Efficient Route to Enantiomerically Enriched Mono- and Diesters of anti-2,4-Dimethylglutaric Acid
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(+/-)-anti-2,4-Dimethylpentanedioic anhydride (rac-1) was converted in good yields and with high enantiomeric excess by an enzyme-catalyzed sequential esterification into the (2R,4R)-monoester 2 and the (2S,4S)-diester ent-3.Best results were obtained with Novozym 435, a lipase from Candida antarctica. - Key Words: Enzymes / Lipases / Pentanedioic anhydrides / Alcoholysis, enantioselective / Esterification, sequential
- Ozegowski, Ruediger,Kunath, Annamarie,Schick, Hans
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p. 215 - 218
(2007/10/02)
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