Lipase-catalyzed synthesis of a tri-substituted cyclopropyl chiral synthon: a practical method for preparation of chiral 1-alkoxycarbonyl-2-oxo-3-oxabicyclo[3.1.0]hexane |
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| Affiliation: | 1. Department of Chemistry, Ryazan State University, 46 Svoboda Street, 390000 Ryazan, Russian Federation;2. European Synchrotron Radiation Facility, B. P. 220, 38043 Grenoble Cedex, France;3. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russian Federation;4. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskiy Prospect 31/4, 119071 Moscow, Russian Federation;5. Department of General Physics, Moscow Institute of Physics and Technology, Institutskii per. 9, 141700 Dolgoprudny, Moscow Region, Russian Federation;1. CSIR-National Chemical Laboratory, Division of Organic Chemistry, Dr. Homi Bhabha Road, Pune 411008, India;2. Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India;1. Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700 032, India;2. Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah 711 103, India;3. Department of Chemistry, National Institute of Technology Agartala, Tripura (W) 799 046, India |
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| Abstract: | An efficient method for the preparation of optically active enantiomers of 1-ethoxycarbonyl-2-oxo-3-oxabicyclo[3.1.0]hexane 1 has been developed. Treatment of 1 with lipase Amano PS gave (1S,5R)-1-carboxy-2-oxo-3-oxabicyclo[3.1.0]hexane 4a which was converted to (1S,5R)-1-ethoxycarbonyl-2-oxo-3-oxabicyclo[3.1.0]hexane 1a with high enantiomeric purity (98.0% ee, 75% yield), while the (1R,5S)-lactone ester 1b remained intact. A simple procedure for the recovery of 4a from the reaction mixture was also established. |
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