Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

• Ákos Bajtel,
• Mounir Raji,
• Matti Haukka,
• Ferenc Fülöp and
• Zsolt Szakonyi

Beilstein J. Org. Chem. 2021, 17, 983–990, doi:10.3762/bjoc.17.80

• the regioisomers of potential monoterpenic 2-amino-1,3-diols [29][30][31][32][33]. These trifunctionalized terpenoids may also possess diverse biological activities and could successfully applied as chiral catalysts in enantioselective transformations [34]. In the present study, our aim was to

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

• derivatives [113], the cyanoborylation of terminal allenes 382 has also been studied. Using B2pin2 in the presence of N-cyano-N-phenyl-p-toluenesulfonamide (NCTs, 377), under Cu-catalysis led to regio-, chemo-, and diastereoselective trifunctionalized products 383–386. The reaction sequence involves three

A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones

• Daniel P. Pienaar,
• Kamogelo R. Butsi,
• Amanda L. Rousseau and
• Dean Brady

Beilstein J. Org. Chem. 2019, 15, 2930–2935, doi:10.3762/bjoc.15.287

• solvents was successfully exploited using inexpensive KOt-Bu to obtain a variety of β-ketonitriles and trifunctionalized building blocks, including useful O-unprotected diols. It was discovered that lactones react to produce the corresponding derivatized cyclic hemiketals. Furthermore, the addition of a

• catalytic amount of isopropanol, or 18-crown-6, was necessary to facilitate the reaction and to reduce side-product formation under ambient conditions. Keywords: acylation; β-ketonitrile; enolizable; trifunctionalized; sustainable; Introduction β-Ketonitriles represent highly versatile intermediates for

• -substituted carboxylic acid derivatives, in general, from cheap commercially available esters, and as such merited further investigation. We required a green, safe and scalable process for the facile production of O-unprotected hydroxylated β-hydroxynitrile 1 via trifunctionalized β-ketonitrile 2 by a direct

Efficient resolution of racemic crown-shaped cyclotriveratrylene derivatives and isolation and characterization of the intermediate saddle isomer

• Sven Götz,
• Andreas Schneider and
• Arne Lützen

Beilstein J. Org. Chem. 2019, 15, 1339–1346, doi:10.3762/bjoc.15.133

• Sven Gotz Andreas Schneider Arne Lutzen Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany 10.3762/bjoc.15.133 Abstract The preparative resolution of a trifunctionalized C3-symmetrical chiral cyclotriveratrylene derivative was