134276-82-7Relevant academic research and scientific papers
Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine
D'Hollander, Agathe C.A.,Westwood, Nicholas J.
supporting information, p. 224 - 239 (2017/12/08)
One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.
Asymmetric total synthesis of paecilomycin E, 10′-epi-paecilomycin e and 6′-epi-cochliomycin C
Pal, Pratik,Jana, Nandan,Nanda, Samik
supporting information, p. 8257 - 8274 (2015/01/08)
The asymmetric total syntheses of naturally occurring resorcylic acid lactone paecilomycin E and two of its structural congeners have been reported in this article. The major highlight of the synthetic venture is the application of the late stage Mitsunob
C2-symmetrical bipyridyldiols as promising enantioselective catalysts in Nozaki-Hiyama allylation
Huang, Xin-Ren,Pan, Xin-Hong,Lee, Gene-Hsian,Chen, Chinpiao
supporting information; experimental part, p. 1949 - 1954 (2011/10/13)
Several new chiral bipyridyldiol ligands that promote the chromium-catalyzed enantioselective addition of allylic halides to aldehydes in up to 99% ee were synthesized. The chromium-catalyzed allylation of aldehydes using ligands 4 and 4a in the presence
Synthetic Approaches to the Alkaloids of the Ancistrocladaceae. Part 3. The Total Synthesis of (-)-Ancistrocladinine: Control of the Diastereoisomer Excess in the Synthesis of Axially Chiral Biaryls.
Rizzacasa, Mark A.,Sargent, Melvyn V.
, p. 2773 - 2782 (2007/10/02)
The total synthesis of the naphthylisoquinoline alkaloid (-)-ancistrocladinine is described.The key step was the construction of the disymmetric bi
