Issue 14, 2006
From the journal:

Organic & Biomolecular Chemistry

Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates†

Edmund J. Keliher,a   Richard C. Burrell,b   Harry R. Chobanian,c   Karina L. Conkrite,d   Rajesh Shuklae  and  John E. Baldwin*f  

* Corresponding authors

a Current address: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Box 234, Cambridge, MA, USA

b Current address: Department of Chemical Synthesis, The Bristol–Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT, USA

c Current address: Department of Medicinal Chemistry, Merck Research Laboratories, Merck and Co. Inc., P.O. Box 2000, Rahway, NJ, USA

d January 2000 Undergraduate Research Intern, Wells College, Aurora, NY, 13026, USA. Current address: Carnegie Institution of Washington, Department of Embryology, 3520 San Martin Drive, Baltimore, MD, USA

e Current address: PCI Synthesis Inc., 9 Opportunity Way, Newburyport, MA, USA

f Department of Chemistry, Syracuse University, Syracuse, New York, USA
E-mail: jbaldwin@syr.edu
Fax: +1-315-443-4070
Tel: +1-315-443-3743

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 α-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl (1S,2S)-2-phenylcyclopropanecarboxylates (the 1-d-3-13C, 1,(3S)-d2, 1,2,(3S)-d3, and 1,3,3-d3 isotopomers) of better than 99% ee have been realized.

Graphical abstract: Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates

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Article information

DOI
https://doi.org/10.1039/B605912K
Article type
Paper
Submitted
26 Apr 2006
Accepted
05 Jun 2006
First published
20 Jun 2006

Org. Biomol. Chem., 2006,4, 2777-2784

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Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates

E. J. Keliher, R. C. Burrell, H. R. Chobanian, K. L. Conkrite, R. Shukla and J. E. Baldwin, Org. Biomol. Chem., 2006, 4, 2777 DOI: 10.1039/B605912K

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