165615-26-9Relevant articles and documents
Benzannulation of 3-substituted pyrroles to indoles
Katritzky, Alan R.,Ledoux, Stephane,Nair, Satheesh K.
, p. 5728 - 5730 (2003)
In a new general indole synthesis, the anion derived from benzotriazolyl derivative 5b underwent regioselective 1,4-addition to various α,β-unsaturated ketones; subsequent acid-catalyzed cyclization formed the corresponding indoles 1a-f.
CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications
Li, Chengxi,Liu, Richard Y.,Jesikiewicz, Luke T.,Yang, Yang,Liu, Peng,Buchwald, Stephen L.
supporting information, p. 5062 - 5070 (2019/03/26)
Chiral tertiary alcohols are important building blocks for the synthesis of pharmaceutical agents and biologically active natural products. The addition of carbon nucleophiles to ketones is the most common approach to tertiary alcohol synthesis but traditionally relies on stoichiometric organometallic reagents that are difficult to prepare, sensitive, and uneconomical. We describe a mild and efficient method for the copper-catalyzed allylation of ketones using widely available 1,3-dienes as allylmetal surrogates. Homoallylic alcohols bearing a wide range of functional groups are obtained in high yield and with good regio-, diastereo-, and enantioselectivity. Mechanistic investigations using density functional theory (DFT) implicate the in situ formation of a rapidly equilibrating mixture of isomeric copper(I) allyl complexes, from which Curtin-Hammett kinetics determine the major isomer of the product. A stereochemical model is provided to explain the high diastereo- and enantioselectivity of this process. Finally, this method was applied to the preparation of an important drug, (R)-procyclidine, and a key intermediate in the synthesis of several pharmaceuticals.
Synthesis and Diels-Alder reactions of the furo[3,4-b]pyrrole ring system. A new indole ring synthesis
Moskalev, Nikolai V.,Gribble, Gordon W.
, p. 197 - 201 (2007/10/03)
The previously unknown furo[3,4-b]pyrrole ring system has been synthesized from the appropriate pyrrolo hydroxyketones by acid-catalyzed cyclodehydration. Diels-Alder reactions of these furo[3,4-b]pyrroles affords a new synthesis of indoles.
Diels-Alder Reactions of 2- and 3-Vinyl-1-(phenylsulfonyl)pyrroles
Xiao, Dong,Ketcha, Daniel M.
, p. 499 - 504 (2007/10/02)
Regioselectively produced 2- and 3-acetyl-1-(phenylsulfonyl)pyrroles can be reduced to the corresponding alcohols and subsequently dehydrated to afford N-protected vinylpyrroles.These remarkably stable vinylpyrroles can then serve as heterodienes in 4 +
