Copper-catalyzed yne-allylic substitutions: concept and recent developments

• Shuang Yang and
• Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

• -ethynylthiophene esters. Proposed mechanism. [4 + 1] annulation of yne-allylic esters and cyclic 1,3-dicarbonyls. Asymmetric [4 + 1] annulation of yne-allylic esters. Proposed mechanism. Asymmetric [3 + 2] annulation of yne-allylic esters. Postulated annulation step. [4 + 1] Annulations of vinyl ethynylethylene

New advances in asymmetric organocatalysis

• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 240–242, doi:10.3762/bjoc.18.28

• nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts are effective under solvent-free conditions [26]. Zhai and Du demonstrated that asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins are efficiently

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• Jiang-Song Zhai Da-Ming Du School of Chemistry and Chemical Engineering, Beijing Institute of Technology, No.5 Zhongguancun South Street, Beijing 100081, People’s Republic of China 10.3762/bjoc.18.3 Abstract Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2

All-carbon [3 + 2] cycloaddition in natural product synthesis

• Zhuo Wang and
• Junyang Liu

Beilstein J. Org. Chem. 2020, 16, 3015–3031, doi:10.3762/bjoc.16.251

• -workers applied the enantioselective [3 + 2] annulation to complete the formal synthesis of (−)-ditryptophenaline (12) [46] (Scheme 7C). The synthesis began with the catalytic asymmetric [3 + 2] annulation of symmetric isoindigo 104 and allene 101 with chiral phosphine catalyst 102 to give spirocyclic

• cycle. (C) Application of phosphine-catalyzed asymmetric [3 + 2] annulation to prepare the chiral adduct 105 with symmetric isoindigo 104 in the formal synthesis of (−)-ditryptophenaline (12). (A) Rhodium-catalyzed intracmolecular [3 + 2] cycloaddition [49]. (B) The proposed catalytic cycle of the

Chiral phosphines in nucleophilic organocatalysis

• Yumei Xiao,
• Zhanhu Sun,
• Hongchao Guo and
• Ohyun Kwon

Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218

• binaphthyl skeleton, Fu and co-workers developed the first asymmetric [3 + 2] annulation of ethyl allenoate with various α,β-unsaturated enones to provide functionalized cyclopentenes (Scheme 2) [35]. The key structural feature of the chiral catalyst B1 is its rigid binaphthyl skeleton. This approach allowed

• moiety, Shi and co-workers developed an asymmetric [3 + 2] annulation of α-substituted acrylates with an allenoate (Scheme 26) [57]. The reactions proceeded smoothly in toluene at room temperature to give the corresponding functionalized cyclopentenes in high yields with moderate to good ee. The

• chiral rhenium-containing phosphine F4 in the asymmetric [3 + 2] annulation of allenoates with N-tosylimines (Scheme 28) [62]. Gratifyingly, this acyclic chiral phosphine could efficiently catalyze this transformation, providing pyrroline derivatives in excellent yields (90–93%), albeit after long

Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides

• Hong-Ping Deng,
• De Wang,
• Yin Wei and
• Min Shi

Beilstein J. Org. Chem. 2012, 8, 1098–1104, doi:10.3762/bjoc.8.121

• of Chemistry & Molecular Engineering, East China University of Science and Technology, and 130 MeiLong Road, Shanghai 200237, People’s Republic of China 10.3762/bjoc.8.121 Abstract We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman

• previous literature. Keywords: asymmetric [3 + 2] annulation; maleimides; Morita–Baylis–Hillman carbonates; multifunctional thiourea-phosphine; organocatalysis; Introduction Highly functionalized cyclopentene derivatives are important subunits in a variety of biologically active molecules and have

• ] annulation catalyzed by chiral phosphines, Zhang and co-workers first reported the asymmetric [3 + 2] annulation of allenoates with acrylates catalyzed by a bicyclic chiral phosphine in 1997 [21]. Moreover, Fu [22][23][24], Marinetti [25][26][27][28], Lu [29][30][31] and other researchers [32][33][34][35][36