Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

• Austin Pounder,
• Eric Neufeld,
• Peter Myler and
• William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

• derivatives 174 (Scheme 31) [77]. The reaction was amenable to a wide range of substituted arylphosphine derivatives. Moreover, the reaction could be extended to include various phosphinate, phosphonate, and phosphonamide derivatives. The use of triarylphosphine oxides required the reaction to be performed at

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts

• Karen R. Winters and
• Jean-Luc Montchamp

Beilstein J. Org. Chem. 2022, 18, 1471–1478, doi:10.3762/bjoc.18.154

• separation of the (S)-1-phenylethylamine-derived phosphonamide diastereoisomers) with SP-3 and RP-3 obtained in 13% and 9% respectively starting from 2,6-diphenylphenol. Finally, N-biphenyl-DOPO CPA 4 was synthesized in four steps as shown in Scheme 4. Although compound 16 is commercially available, it was

• synthesized from 2-aminobiphenyl according to the literature [47]. Subsequent reaction with phosphorus trichloride and electrophilic aromatic substitution gave a chlorophosphine intermediate, which was directly reacted with (S)-1-phenylethylamine, then hydrogen peroxide. Phosphonamide diastereoisomers 17 were

Organophosphorus chemistry

• Paul R. Hanson

Beilstein J. Org. Chem. 2014, 10, 2087–2088, doi:10.3762/bjoc.10.217

• inhibitors. More specifically, the Thematic Series spans new methods in C–P bond formation, chiral phosphines in nucleophilic organocatalysis, chiral N-phosphinyl auxiliaries, cyclic phosphonamide reagents in the total synthesis of natural products, phosphinate-containing heterocycles, new routes to

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

• bioactive compounds adopting phosphonamide anion technology is presented highlighting the utility of phosphonamide reagents in stereocontrolled bond-forming reactions. Methodologies utilizing phosphonamide anions in asymmetric alkylations, Michael additions, olefinations, and cyclopropanations will be

• summarized, as well as an overview of the synthesis of the employed phosphonamide reagents. Keywords: conjugate addition; cyclopropanation; olefination; organophosphorus; phosphonamide; total synthesis; Introduction Chiral non-racemic and achiral cyclic phosphonamide reagents 1–7 (Figure 1) have been

• and complex natural products and also of biologically active compounds. The phosphonamide anions are derived from a small number of common motifs as shown in Figure 1. Diazaphospholidine 2 was introduced by Hanessian and co-workers, and represents the most commonly used phosphonamide in organic