In an article, author is Smith, Isaac T., once mentioned the application of 611-71-2, Quality Control of (R)-2-Hydroxy-2-phenylacetic acid, Name is (R)-2-Hydroxy-2-phenylacetic acid, molecular formula is C8H8O3, molecular weight is 152.1473, MDL number is MFCD00064251, category is indole-building-block. Now introduce a scientific discovery about this category.
Synthesis of pyrroloindolines through formal [3+2]-cycloaddition of indoles with chiral N-2-acetamidoacrylyl oxazolidinones
Chiral N-2-acetamidoacrylyl oxazolidinones were produced and reacted with indoles under Lewis acid conditions to generate hexahydropyrrolo[2,3-b]indole products in a formal [3 + 2] cycloaddition process. Optimal conditions included the use of tin(IV) chloride in methylene chloride at 0 degrees C. Pyrroloindoline products were obtained from various indoles with shorter reaction times (12 hr) up to 91% yield with high, >20:1 exo selectivity. A mechanism involving reversible conjugate addition followed by an enamine lone-pair-iminium capture, tautomerization, and tin-enolate protonation accounts for the selectivity. The method enables selective applications to pyrroloindoline targets and further refinement with chiral catalysts. (C) 2020 Elsevier Ltd. All rights reserved.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles