Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates |
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| Authors: | Keliher Edmund J Burrell Richard C Chobanian Harry R Conkrite Karina L Shukla Rajesh Baldwin John E |
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| Affiliation: | Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Box 234, Cambridge, MA 02138, USA. |
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| Abstract: | Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with alpha-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl (1S,2S)-2-phenylcyclopropanecarboxylates (the 1-d-3-(13)C, 1,(3S)-d2, 1,2,(3S)-d3, and 1,3,3-d3 isotopomers) of better than 99% ee have been realized. |
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