Paper containing our reaction: Gong, J.; Lin, G.; Sun, W.; Li, C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 16745–16746.
Paper cited in our reaction: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. J. Org. Chem. 1996, 61, 88.
In our reaction, oxidative arylation occurs to create a ketoester. This ketoester was then tested with a variety of reagents in hopes of finding a selective and high-yielding reagent that would give the desired, reduced product. Direct reaction with a hydride reducing agent gave a poor yield of the desired stereoselective product, so researchers decided to try and produce a larger yield of the desired product in a 2-step process. Our paper cited “Chiral Synthesis via Organoboranes. 42. Selective Reductions. 57. Efficient Kinetic Resolution of Representative alpha-Tertiary Ketones with beta-Chlorodiisopinocamphenylborane,” because it outlines a successful stereoselective synthesis of a product using organoboranes, and because of this, the researchers decided to try to use organoboranes in the first step in this 2-step reducing process as a way to get a high yield of the desired diastereomer. However, they found that the intermediate, and therefore also the product that the organoboranes mostly produced, was the undesired diastereomer. The researchers ended up using a material other than organoboranes to get the desired product.
Papers that also cited Ramachandran et al., 1996:
1.) “Catalytic Asymmetric Intramolecular Homologation of Ketones with alpha-Diazoesters: Synthesis of Cyclic alpha-Aryl/alkyl beta-Ketoesters”
This paper involves the synthesis of a ketoester from at least one aryl ring, similar to our reaction. It also cites the paper by Ramachandran et al., 1996, because the researchers attempted to use organoboranes as a way to form a specific stereoselective product.
Li, W.; Tan, F.; Hao, X.; Wang, G.; Tang, Y.; Liu, X.; Lin, L.; Feng, X. Chem. Int. Ed. 2015, 54, 1608–1611.
2.) “Synthesis and [4+2] Cycloaddition of (2R,2′R)-N,N′-Fumaroylbis[fenchane-8,2-sultam] (=(2E)-1,4-Bis[(3aS,6S,7aR)-1,4,5,6,7,7a-hexahydro-7,7-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzothiazol-1-yl]but-2-ene-1,4-dione) to Cyclopentadiene”
This paper discusses the formation of a certain product and the Diels Alder Reaction that a certain conformation of that product can undergo. It says that methylnorcamphor can be used as an interesting substitute to the major testing material (fenchone), which is information that they got from Ramachandran et al., 1996.
Piątek, A.M.; Chojnacka, A.; Chapuis, C.; Jurczak, J. HCA 2005, 88, 2441–2453.
3.) “Influence of norbornanone substituents on both the Wagner–Meerwein skeletal rearrangements under sulfonation conditions and the diastereoselectivity of the corresponding N,N′-bis-fumaroyl sultams in uncatalyzed Diels–Alder cycloadditions to cyclopenta-1,3-diene”
This paper also cites Ramachandran et al., 1996 because it discusses the use of (1R,4S)-1-methyl-2-norbornanone in creating the desired, stereoselective product. As indicated, the (1R,4S)-1-methyl-2-norbornanone allowed for the isolation of sulfonic acid.
Piątek, A. M.; Chapuis, C. Tetrahedron 2013, 54, 4247-4249.
