Journal ArticleDOI
Sequential One-Pot InBr3-Catalyzed 1,4- then 1,2-Nucleophilic Addition to Enones
Marco Bandini,Pier Giorgio Cozzi,Massimo Giacomini,Paolo Melchiorre,Simona Selva,Achille Umani‐Ronchi +5 more
TLDR
With the optimized atom-efficient protocol, several polyfunctionalized alpha-silyloxy cyanohydrins were synthesized in good to excellent yields and a notable level of simple 1,3-diastereoselection was recorded in the case of 2-cyclohexen-1-one 2c.Abstract:
Low sensitivity toward traces of moisture and high tolerance of different functional groups make indium tribromide suitable for carrying out multistep synthetic sequences. In particular, we have realized a 1,4-conjugated addition of indoles/thiols to α,β-unsaturated ketones mediated by a catalytic amount (10 mol %) of InBr3 obtaining the desired β-substituted ketones in good yields. The Lewis acidity of indium salts was not affected by coordinating and acid nucleophiles; therefore, the subsequent catalytic 1,2-addition of Me3SiCN to carbonyl compounds can be performed in one pot. With the optimized atom-efficient protocol, several polyfunctionalized α-silyloxy cyanohydrins were synthesized in good to excellent yields (up to 97%) and a notable level of simple 1,3-diastereoselection (up to 84:16) was recorded in the case of 2-cyclohexen-1-one 2c.read more
Citations
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Journal ArticleDOI
Catalytic Functionalization of Indoles in a New Dimension
Marco Bandini,Astrid Eichholzer +1 more
TL;DR: This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.
Journal ArticleDOI
Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals
Journal ArticleDOI
Bismuth Nitrate-Catalyzed Versatile Michael Reactions†
Neeta Srivastava,Bimal K. Banik +1 more
TL;DR: Bismuth nitrate-catalyzed versatile Michael reaction was developed to reduce the complications that characterize the current standard Michael reaction and used for facile preparation of organic compounds of widely different structures.
Journal ArticleDOI
Katalytische Funktionalisierung von Indolen in einer neuen Dimension
Marco Bandini,Astrid Eichholzer +1 more
TL;DR: In this paper, the Fortschritte hinsichtlich der selektiven katalytischen Funktionalisierung von Indolen (durch C-C-Kupplung) aus den vergangenen vier Jahre zusammen.
References
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TL;DR: This retrospective on total synthesis should serve to demonstrate how far the authors have come, yet show that the science of total synthesis is still in its infancy.
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Addition of aromatic thiols to conjugated cycloalkenones, catalyzed by chiral beta-hydroxy amines - a mechanistic study on homogeneous catalytic asymmetric-synthesis
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TL;DR: In contrast to enantioselective alkyl transfer reactions, the corresponding arylations have not yet reached a high level of maturity as discussed by the authors, and existing protocols are either of no general applicability or are limited in terms of selectivity.
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General Procedure for the Synthesis of α-Amino Phosphonates from Aldehydes and Ketones Using Indium(III) Chloride as a Catalyst
TL;DR: In this article, a simple, efficient, and general method was developed for the synthesis of α-amino phosphonates through a one-pot reaction of aldehydes and ketones with amines in the presence of indium(III) chloride as a catalyst.
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Indium(III) Chloride-Promoted Rearrangement of Epoxides: A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones
Brindaban C. Ranu,Umasish Jana +1 more
TL;DR: In this article, a simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed, which provides a highly selective synthesis of substituted benzylic aldehydes and ketones.