Catalytic multi-step domino and one-pot reactions

• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

• stereocenters [7]. In the Review paper by Kisszékelyi and Šebesta, the diverse variety of chiral metal enolates obtained by asymmetric conjugate additions of organometallic reagents and the possibilities to engage metal enolates in tandem reactions with new electrophiles are presented [8]. A Perspective from X

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

• Nosheen Beig,
• Varsha Goyal and
• Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

• , Me, C≡C-n-hep, Ph, CO2Me) and trialkylaluminum (alkyl = Me, Et, iBu) were used for the reactions. This approach is particularly attractive for asymmetric conjugate additions to pentenones, which are otherwise difficult to accomplish. 2.2.3 Reaction with organoboron reagents: In 2010, Hoveyda and co

Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors

• Brigita Mudráková,
• Renata Marcia de Figueiredo,
• Jean-Marc Campagne and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 881–888, doi:10.3762/bjoc.19.65

• excellent in asymmetric conjugate additions of dialkylzincs to acylimidazoles [25]. The initial reaction conditions were inspired by literature precedence on conjugate additions. As the first electrophile for trapping of the chiral enolate, we have used tropylium bistriflimide (Scheme 2). Following our

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

• organic synthetic transformations. Chiral metal enolates obtained by asymmetric conjugate additions of organometallic reagents are structurally complex intermediates that can be employed in many transformations. In this review, we describe this burgeoning field that is reaching maturity after more than 25

• were successfully employed in asymmetric conjugate additions (ACA) [3][4][5][6][7][8][9], mainly organozinc [10], Grignard [11][12][13], trialkylaluminum [14], or organozirconium reagents [15]. Additions with these reagents lead to corresponding zinc, magnesium, aluminum, and zirconium enolates, which

• conjugate additions of Grignard reagents. At the outset of our studies, there were works in which dialkylzinc additions were utilized to generate zinc enolates, and these enolates were then trapped with chiral sulfonylimines [24]. Specifically, we asked whether these magnesium enolates could be trapped with

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones

• Jan Bartáček,
• Jan Svoboda,
• Martin Kocúrik,
• Jaroslav Pochobradský,
• Alexander Čegan,
• Miloš Sedlák and
• Jiří Váňa

Beilstein J. Org. Chem. 2021, 17, 1048–1085, doi:10.3762/bjoc.17.84

• excellent both in terms of enantioselectivities and conversions (up to 98%; up to 83% ee; Table 28). The reuse of the heterogeneous catalyst has not been studied in this case. In 2020, our group reported the first heterogeneous polystyrene-supported recyclable catalyst for the asymmetric conjugate additions

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

• Delphine Pichon,
• Jennifer Morvan,
• Christophe Crévisy and
• Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

• -acyloxazolidinones, N-acylpyrrolidinones, amides, and N-acylpyrroles have been scarcely investigated in Cu ECA despite their usefulness for postfunctionalizations. This tutorial review aims to describe the early examples and recent advances in copper-catalyzed asymmetric conjugate additions of dialkylzinc, Grignard

• ]. Indeed, due to their poor reactivity compared to other Michael acceptors, catalytic asymmetric conjugate additions of organometallic reagents to N,N-dialkylenamides remained a real challenge. However, thanks to the synergistic action of the boron-based Lewis acid BF3∙Et2O, CuBr∙SMe2, and the chiral (R,S

Conjugate addition–enantioselective protonation reactions

• James P. Phelan and
• Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

• . Building on his asymmetric conjugate additions to α-substituted enones, Luo demonstrated that Hantzsch ester 133 chemoselectively reduces activated alkenes 132 in the presence of α-substituted vinyl ketones 118, generating carbon nucleophiles 135 in situ. These nucleophiles then reacted with the α

Copper-catalysed asymmetric allylic alkylation of alkylzirconocenes to racemic 3,6-dihydro-2H-pyrans

• Emeline Rideau and
• Stephen P. Fletcher

Beilstein J. Org. Chem. 2015, 11, 2435–2443, doi:10.3762/bjoc.11.264

• ][17][18]. We have developed Cu-catalysed asymmetric conjugate additions of alkylzirconium reagents generated in situ by hydrometallation of terminal alkenes [19][20][21][22][23][24][25], and recently demonstrated that zirconium nucleophiles may undergo highly enantioselective copper-catalysed AAAs to

Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

• Thibault E. Schmid,
• Sammy Drissi-Amraoui,
• Christophe Crévisy,
• Olivier Baslé and
• Marc Mauduit

Beilstein J. Org. Chem. 2015, 11, 2418–2434, doi:10.3762/bjoc.11.263

• provided dramatic breakthroughs during the last two decades. This review aims to describe the early examples and recent advances in copper-catalyzed asymmetric conjugate additions of organometallic reagents to extended Michael acceptors. First, seminal reports dealing with the reactivity of extended

• allowing 3 to 4 sequential ACA reactions would be highly desirable for synthetic chemists. Conclusion This review attempts to give the reader an overview of the methodologies available to perform regio- and enantioselective copper-catalyzed asymmetric conjugate additions (ACA) on electron-deficient

Copper catalysis in organic synthesis

• Sherry R. Chemler

Beilstein J. Org. Chem. 2015, 11, 2252–2253, doi:10.3762/bjoc.11.244

• Ullmann and Goldberg couplings, asymmetric acetylide additions to carbonyl groups, radical alkylations and asymmetric conjugate additions as well as original contributions in the area of copper-catalyzed C–C cross-coupling, conjugate additions, allylic alkylations, alkene difunctionalizations, heterocycle

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• ][40]. Asymmetric conjugate additions using P-chiral phosphonamides were reported by Denmark [2][3][4] and Hua [5][6], with remarkable differences in selectivity depending on the configuration of the P-stereogenic center (Scheme 5). Thus, the addition of the Li-anion of trans-40a to cyclic enones 41

Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts

• Saet Byeol Woo and
• Dae Young Kim

Beilstein J. Org. Chem. 2012, 8, 699–704, doi:10.3762/bjoc.8.78

• to the development of asymmetric conjugate additions of 1,3-dicarbonyl compounds to various Michael acceptors [27][28][29][30][31][32][33]. Recently, the groups of Du and Zhou reported a highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by chiral

An exceptional P-H phosphonite: Biphenyl- 2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper- catalyzed 1,4-additions

• T. Kop-Weiershausen,
• J. Lex,
• J.-M. Neudörfl and
• B. Goldfuss

Beilstein J. Org. Chem. 2005, 1, No. 6, doi:10.1186/1860-5397-1-6

• -catalyzed 1,4-additions of ZnEt2 to 2-cyclohexen-1-one, this P-H phosphonite (yielding 65% ee) exceeds even the corresponding phosphite and phosphoramidite. Keywords: phosphorus ligands; chirality; biaryls; asymmetric conjugate additions; phosphoramidites; phosphites; phosphonites; X-ray analyses

• ][13][14][15][16][17][18] Such asymmetric conjugate additions of diethylzinc to enones are often highly enantioselective, especially with phosphoramidites (amidophosphites) and phosphites. [2][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41] These chiral