Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions

• Yonglei Du,
• Jian Li,
• Kerong Chen,
• Chenglin Wu,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2017, 13, 1342–1349, doi:10.3762/bjoc.13.131

• stereocenters and a unique quaternary stereogenic center, with good yields, and excellent diastereoselectivity and enantioselectivity using thiourea-catalyzed Michael–Henry cascade reactions. We anticipate that this reaction will simplify the synthesis of complex spirooxindoles containing multiple chiral

• centers with potential pharmacological properties. Experimental General procedure for the synthesis of products (3a–j): To a mixture of 1a–j (0.11 mmol) and 2a (0.1 mmol) in CH2Cl2 (3 mL) was added catalyst d (0.01 mmol). Then the mixture was stirred at −20 °C for 12 h. After completion of the reaction

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

• Dimpee Gogoi,
• Runjun Devi,
• Pallab Pahari,
• Bipul Sarma and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

• of two or more privileged scaffolds leads to geometrically well-defined rigid polycyclic structures with enhanced receptor-binding selectivity. Thus, the design and synthesis of structurally diverse, privileged structure-based polycyclic molecules with multiple chiral centers has been intensely

Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter

• Sara Meninno,
• Chiara Volpe,
• Giorgio Della Sala,
• Amedeo Capobianco and
• Alessandra Lattanzi

Beilstein J. Org. Chem. 2016, 12, 643–647, doi:10.3762/bjoc.12.63

• bearing multiple chiral centers increased over the last years [1]. Indeed, chiral non-racemic functionalized tetrahydrothiophenes are endowed with different biological activities [2][3][4][5] and they are useful ligands in asymmetric catalysis [6]. However, few asymmetric approaches are available to

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

• Giorgos Koutoulogenis,
• Nikolaos Kaplaneris and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2016, 12, 462–495, doi:10.3762/bjoc.12.48

• main tools a synthetic chemist has to perform asymmetric catalysis. In this review the synthesis of six-membered rings, that contain multiple chiral centers, either by a ring closing process or by a functionalization reaction on an already existing six-membered ring, utilizing bifunctional (thio)ureas

• products, pharmaceuticals and agrochemicals, thus, a lot of effort has been put by the synthetic community to provide mild, reliable, robust and operationally simple methods to construct them. Of the vast variety of six-membered rings, those with multiple chiral centers pose the most difficult synthetic

• challenge, because not only the regiochemical outcome, but also the stereochemical outcome of the reaction must be carefully controlled. Since its rebirth, organocatalysis has made many contributions in the synthesis of six-membered rings with multiple chiral centers, this area has been reviewed in the past

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

• Guijun Wang,
• Hao Yang,
• Sherwin Cheuk and
• Sherman Coleman

Beilstein J. Org. Chem. 2011, 7, 234–242, doi:10.3762/bjoc.7.31

• because they are naturally abundant and possess multiple chiral centers that can be selectively functionalized [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37]. Sugar-based supramolecular hydrogels are being explored as biocompatible soft materials and as