Asymmetric synthesis of a stereopentade fragment toward latrunculins

• Benjamin Joyeux,
• Antoine Gamet,
• Nicolas Casaretto and
• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 428–433, doi:10.3762/bjoc.19.32

• oxidation in presence of DMP. The assembly of aldehyde 8 and methyl ketone 15 was envisaged through a stereoselective aldol reaction. After unsuccessful attempts of Mukaiyama aldol reactions with silyl enol ethers [28], we found that dicyclohexylboron enolate 20, made in situ from ketone 15 and Cy2BCl in

• -citronellene (10). Synthesis of fragment 8 from ʟ-cysteine ethyl ester hydrochloride (16). Synthesis of fragment 21 through a stereoselective aldol reaction. 1,3-Anti-diastereoselective reduction of 21 with PNBz transposition, and final determination of the relative stereochemistry by NOESY experiment on 25

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

• Pierre-Antoine Nocquet,
• Aurélie Macé,
• Frédéric Legros,
• Jacques Lebreton,
• Gilles Dujardin,
• Sylvain Collet,
• Arnaud Martel,
• Bertrand Carboni and
• François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

• -protected aldehyde should afford the desired aldol adduct with a syn relative configuration between the two newly created chiral centers [29][30]. Moreover, the boron-mediated stereoselective aldol reaction is all the more interesting for our synthetic plan as stereochemical diversity can be generated

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

• Myriam Drouin and
• Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

• protection. Xaa-ψ[CF=C]-Pro The first asymmetric synthesis of Xaa-ψ[CF=C]-Pro was reported in 2012 by Chang’s group with the synthesis of MeOCO-Val-ψ[(Z)-CF=C]-Pro 93 (Scheme 18) [52]. Their synthesis started with a stereoselective aldol reaction using (L)-threonine to furnish a chiral β-hydroxy

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

• Davide Brenna,
• Elisabetta Massolo,
• Alessandra Puglisi,
• Sergio Rossi,
• Giuseppe Celentano,
• Maurizio Benaglia and
• Vito Capriati

Beilstein J. Org. Chem. 2016, 12, 2620–2626, doi:10.3762/bjoc.12.258

• . Keywords: continuous process; DES; organocatalysis; proline; stereoselective aldol reaction; Introduction The aldol reaction is a powerful synthetic tool to create new C–C bonds [1]. It offers several possibilities to control the stereochemical outcome of the process and to afford stereochemically defined

• stereoselective aldol reaction in DES. Aldol reaction under continuous flow conditions in DESs. ChCl-based eutectic mixtures used in the present work. DES screening for the proline-catalyzed in batch aldol reaction. Three different set-ups for the aldol reaction in continuo. In continuo aldol reactions of