"I just moved to Paris, I'm taking some chemistry [classes] there and I've been there for about three weeks and when I get back there I'm going to be looking for some chemistry references [agencies]".
- McKey Sullivan (Cycle 11)
A. Reference
Green, J. E.; Bender, D. M.; Jackson, S.; O'Donnell, M. J.; McCarthy, J. R. Org. Lett., 2009, 11, 807-810.
The researchers transformed chiral tertiary α-hydroxy esters to α-azido esters by the Mitsunobu reaction with HN3. There was complete inversion of configuration at the α-carbon. In the Fukuyama paper, there was also an inversion of stereochemistry from the reactant (benzyl 2-((5R,6S)-5-(tert-butyldimethylsilyloxy)-6-hydroxycyclohex-1-enyl)ethylcarbamate) to the product (benzyl 2-((5R,6R)-5-(tert-butyldimethylsilyloxy)-6-(3-(2,2-dimethoxyethyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethylcarbamate) using the Mitsunobu reaction. The Mitsunobu reaction is used to allow the conversion of primary or secondary alcohols to esters, phenyl esters, thioethers…etc. through the mechanism with the reagents, such as DEAD (diethylazodiacarboxylate) in an “SN2” reaction, which results in the inversion of stereochemistry.
B. Paper #1
Armstrong, A.; Emmerson, D. P. G. Org. Lett. 2011, 1040-1043.
This paper cited the paper chosen in order to give the reader a review of asymmetric synthesis of R,R-disubstituted Ramino Acids which occurred in their reaction.
C. Paper #2
Misaki, T.; Takimoto, G.; Sugimura, T. J. Am. Chem. Soc. 2010, 132, 6286-6287.
This paper used the paper chosen to reference, or give explanation or reasoning for the absolute configuration of 5p (one of their products) was determined by conversion into the known α, β-dihydroxyester.
D. Paper #3
Lu, T. J.; Lin, C. K. J. Org. Chem. 2011, 76, 1621–1633.
It used the paper as one of the references to explain the synthesis of optically active, unnatural nonproteinogenic R, R-dialkyl-R-amino acids.
Ege, Seyhan. Organic Chemistry: Structure and Reactivity, 5th ed. New York: Houghton Mifflin Company, 2004; pp. 1-1164.
Organic Chemistry Portal. Mitsunobu Reaction. 1 Apr. 2008. http://www.organic-chemistry.org/namedreactions/mitsunobu-reaction.shtm (accessed March 23, 2011).
Harwood, Laurence M., and Timothy D. Claridge. Introduction to Organic Spectroscopy, 8th ed. New York: Oxford UP, 2005; pp. 1-92.
Koizumi, H.; Yokoshima, S.; Fukuyama, T. Chem. Asian. J. 2010, 5, 2192-2198.
University of Colorado, Boulder. Lab Techniques. 2010. http://orgchem.colorado.edu/hndbksupport/irtutor/aromaticsir.html (accessed April 2, 2011).
Wikipedia. High-performance liquid chromatography. 2011. http://en.wikipedia.org/wiki/High-performance_liquid_chromatography (accessed April 5, 2011).
Nic, M.; Jirat, J.; Kosata, B. Compendium of Chemical Terminology, 2nd ed. Blackwell Scientific Publications. Oxford, 1997.
Chiral Technologies Inc. Laboratory Products and Services for Chiral Analysis and Separation, Pamphlet, Daicel Chemical Industries, LTD, 2006; pp. 1-7.
Sun, F. Mass Spectrometry Laboratory: Electrospray Ionization. http://www.scs.illinois.edu/massSpec/ion/esi.php (accessed April 5, 2011).
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