Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

• Alemayehu Gashaw Woldegiorgis and
• Xufeng Lin

Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185

• scaffold for a variety of natural products, bioactive compounds and pharmacological agents [79] as well as for a variety of chiral phosphine ligands [80]. As a result, the preparation of axially chiral arylpyrroles has been one of the most important areas of investigation in synthetic chemistry. In the

Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position

• Yongsu Li,
• Bendu Pan,
• Xuefeng He,
• Wang Xia,
• Yaqi Zhang,
• Hao Liang,
• Chitreddy V. Subba Reddy,
• Rihui Cao and
• Liqin Qiu

Beilstein J. Org. Chem. 2020, 16, 966–973, doi:10.3762/bjoc.16.85

• efficient synthesis of this scaffold [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22], like Hiyama [23][24], Negishi [25][26] or Suzuki–Miyaura couplings [27][28][29][30][31][32][33][34][35][36]. In these synthetic strategies, the reaction system of palladium with chiral phosphine ligands was

• acid. A gram-scale reaction of 1h with 2a went well and provided 3h with a slightly reduced yield and ee (75% yield and 73% ee, Scheme 3), compared with 3h in Scheme 1. According to the coordination of axial chiral phosphine ligands [65][66] and our analysis, we propose a possible intermediate

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• planar chiral P,N-paracyclophane phosphine ligand 132 with a relatively low yield (42%). The [2.2]paracyclophane has proved to be an important support for planar chiral phosphine ligands. The ligands are generally rigid crystalline compounds that are stable in both high and low pH media and thermally

Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc

• Kohsuke Aikawa,
• Kohei Yabuuchi,
• Kota Torii and
• Koichi Mikami

Beilstein J. Org. Chem. 2018, 14, 576–582, doi:10.3762/bjoc.14.44

• ) groups in good-to-high yields and enantioselectivities. Axial backbones and substituents on phosphorus atoms of chiral phosphine ligands critically influence the enantioselectivity. Moreover, the methylation of simple perfluoroalkylated ketones is found to be facilitated by only chiral phosphines without

• enantioselectivities, and (CuOTf)·C6H6 and CuI led to a racemic product (Table 1, entries 2–4). Chiral phosphine ligands instead of BINAP were further assayed with the aim of enhancing the enantioselectivity. Indeed, the investigation of the effect of axial backbones and substituents on the phosphorus atoms led to an

Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

• Marina Rubina,
• William M. Sherrill,
• Alexey Yu. Barkov and
• Michael Rubin

Beilstein J. Org. Chem. 2014, 10, 1536–1548, doi:10.3762/bjoc.10.158

• the isomerization were identified. It was shown that the nature of this isomerization is different from that demonstrated previously using chiral diphosphine ligands. Keywords: asymmetric catalysis; chiral phosphine ligands; cyclopropane; Heck reaction; organophosphorus; transition metal catalysis

Silver and gold-catalyzed multicomponent reactions

• Giorgio Abbiati and
• Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

• chiral phosphine ligands and AgOAc via bidentate chelation of a properly substituted aldimine. Chiral phosphine–silver(I) complexes are emerging as a valuable tool for carbon–carbon bond forming reactions. These catalysts are effective in promoting enantioselective allylations, aldol reactions, Mannich