The original reference that we had was "Preparation and use of tetra-normal-butylammonium per-ruthenate (TBAP reagent) and tetra-normal-propylammonium per-ruthenate (TPAP reagent) as new catalytic oxidants for alcohols"
Griffith, W. P.; Ley, S.V.; Whitcombe, G.P.; White, A.D. J. Am. Chem. Soc. 1987, 21, 1625-1627.
This article talks about the high yield conversion of alcohols to aldehydes and ketones by a specific method. The specific reagents that are discussed in this article is Tetra-n-butylammonium per-ruthenate (Bun4N)(RuO4) (TBAP) and tetra-n-propylammonium per-ruthenate (Prn4N)(RuO4) (TPAP), with N-methylmorphonline N-oxide(NMO). The article starts by talking about many problems with other oxidation reagents. It also talks about how the TBAP and TPAP were synthesized. The literature ends with saying that TPAP is produced much easier, therefore it is better than TBAP. Our article uses this information to perform oxidation at an alcohol with TPAP and NMO.
Concise enantioselective synthesis of abscisic acid and a new analogue
Smith, T. R.; Clark, A. J.; Clarkson, G. J.; Taylor, P. C.; Marsh, A. Org. Biomol. Chem. 2006, 4, 4186-4192.
This paper also used the above article in a similar way compared to the original Nicolaou article. This article talks about a simple and high yielding synthetic pathway for synthesizing enantiomerically pure (S)-(+) and (R)-( -) abscisic acid. The key intermediates then recrystallize as single diastereoisomers for each enantiomer. TATP and NMO is used in a similar way in this reaction when compared to how it is used for the original Nicolaou article. It is used to go from molecule 10 to molecule 11. One difference is that TATP and NMO are used to oxidize the alcohol group into a aldehyde. This is one key difference. Also, by looking at this reaction we can see another difference. There is another 3º alcohol that does not get oxidized. Because of this, we can conclude that that TATP and NMO cannot oxidize 3º alcohols. One way that this article is different from the original Nicolaou article is that in the Nicolaou article another functional group reacts with the ketone after it is formed. In this article the aldehyde does not react with any other sites on the molecule.
Concise enantioselective synthesis of abscisic acid and a new analogue
Smith, T. R.; Clark, A. J.; Clarkson, G. J.; Taylor, P. C.; Marsh, A. Org. Biomol. Chem. 2006, 4, 4186-4192.
This paper also used the above article in a similar way compared to the original Nicolaou article. This article talks about a simple and high yielding synthetic pathway for synthesizing enantiomerically pure (S)-(+) and (R)-( -) abscisic acid. The key intermediates then recrystallize as single diastereoisomers for each enantiomer. TPAP and NMO is used in a similar way in this reaction when compared to how it is used for the original Nicolaou article. It is used to go from molecule 10 to molecule 11. One difference is that TPAP and NMO are used to oxidize the alcohol group into a aldehyde. This is one key difference. Also, by looking at this reaction we can see another difference. There is another 3º alcohol that does not get oxidized. Because of this, we can conclude that that TPAP and NMO cannot oxidize 3º alcohols. One way that this article is different from the original Nicolaou article is that in the Nicolaou article another functional group reacts with the ketone after it is formed. In this article the aldehyde does not react with any other sites on the molecule.
References with description