Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• selectivity of ortho-lithiation could be tuned by changing the alkyllithium reagent employed. The performance of four inherently chiral bidentate calix[4]arene ligands in the asymmetric Tsuji–Trost allylation reaction (Scheme 10) has been evaluated and compared to that of the planar model ligands. Inherently

• applied in the palladium-catalyzed Tsuji–Trost allylation reaction. BINOL-derived calix[4]arene-diphosphite ligands. Inherently chiral calix[4]arene 43 containing a diarylmethanol structure. Calix[4]arene-based chiral primary amine–thiourea catalysts. Novel prolinamide organocatalysts based on the calix[4

Highly selective palladium–benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions

• Antonio Monopoli,
• Pietro Cotugno,
• Carlo G. Zambonin,
• Francesco Ciminale and
• Angelo Nacci

Beilstein J. Org. Chem. 2015, 11, 994–999, doi:10.3762/bjoc.11.111

• -2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji–Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst

• cooperative catalysis has been also described for the Tsuji–Trost allylation, in which the use of a base in combination with a Pd species resulted in better outcomes [14][15][16][17][18][19][20][21]. However, some of these protocols suffer for severe drawbacks such as long reaction times [18][22], undesirable

• , as a precatalyst in the Tsuji–Trost allylation of active methylene compounds using carbonates as allylating agents (Scheme 1). Results and Discussion Allylic carbonates are suitable reagents for the Tsuji–Trost allylation as they enable to work under neutral conditions. The base required for

Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space

• Simon A. Herbert,
• Laura J. van Laeren,
• Dominic C. Castell and
• Gareth E. Arnott

Beilstein J. Org. Chem. 2014, 10, 2751–2755, doi:10.3762/bjoc.10.291

• examined as ligands in the palladium-catalyzed Tsuji–Trost allylation reaction, returning results comparable to their planar chiral ferrocene counterparts pointing towards future application of these types of compounds. Keywords: calix[4]arene; inherently chiral; ortholithiation; oxazoline; Tsuji–Trost

• to synthesize inherently chiral calixarenes and the surprising reversal of diastereoselectivity obtained when a different alkyllithium was employed. We also wish to report a preliminary study on the application of inherently chiral calix[4]arenes in the classic asymmetric Tsuji–Trost allylation

• calixarenes 5–8, we noted their similarity to planar chiral thioether oxazoline ferrocene ligands (9 in Figure 1) already reported by Dai and co-workers [35]. We therefore initiated a pilot study with our inherently chiral calix[4]arenes, using the palladium-catalyzed Tsuji–Trost allylation reaction (Scheme 3

Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ₀)

• Sabin Llona-Minguez and
• Simon P. Mackay

Beilstein J. Org. Chem. 2014, 10, 1333–1338, doi:10.3762/bjoc.10.135

• developed by Springthorpe et al. [32], we then investigated a route to prepare the enantiopure (1S,2R,3S,4R)-4-aminocyclopentane-1,2,3-triol analogue of PreQ0 16 (Figure 5). The first step is a Tsuji–Trost allylation of sodium di-tert-butyliminodicarboxylate. The reaction proceeded with an overall retention

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

• Sebastian Krüger and
• Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

• underwent DVCPR to give cyclohexane 216. Tsuji–Trost allylation [176][177] furnished the quartenary carbon center. A two-step Fischer-indole strategy [178][179] finished tetracycle 217 under forcing conditions. Takeda and coworkers [180] set out to investigate the use of an anionic oxy-cis

Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation

• Lynnie Trzoss,
• Jing Xu,
• Michelle H. Lacoske and
• Emmanuel A. Theodorakis

Beilstein J. Org. Chem. 2013, 9, 1135–1140, doi:10.3762/bjoc.9.126

• –Miescher ketones represent two of the most famous examples [59][60][61][62][63][64][65]. With this background information in mind, we devised an enantioselective synthesis of 8 starting from commercially available dione 12, and the synthesis of 8 was previously published [25][26]. Tsuji–Trost allylation