93176-40-0

Upstream product

• 32623-19-1 4-(4'-Methylphenyl)-4-pentenal 
• 930-30-3 cyclopent-2-enone 
• 5720-05-8 4-methylphenylboronic acid 
• 22627-70-9 3-ethoxycyclopent-2-en-1-one 
• 3859-41-4 1,3-cyclopentadione 
• 65564-87-6 3-(4-Methylphenyl)-2-cyclopenten-1-one 
• 128860-65-1 4-bromo-4-pentenal dimethyl acetal 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 36884-29-4 4-bromo-pent-4-enal 
• 106-38-7 para-bromotoluene 
• 93366-59-7 (S)-(+)-2-(p-anisylsulfinyl)-2-cyclopentenone 
• 93366-60-0 6-((S)-4-Methoxy-benzenesulfinyl)-1,4-dioxa-spiro[4.4]non-6-ene 

Relevant academic research and scientific papers

Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?

The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones

Chiral N-aryl sulfinamide-olefins which are readily synthesized via C-N coupling and nucleophilic substitution have been used as chiral ligands, which demonstrate moderate to excellent asymmetric catalytic performance in the rhodium-catalyzed asymmetric 1

Developing Chiral Dibenzazepine-Based S(O)-Alkene Hybrid Ligands for Rh(I) Complexation: Catalysts for the Base-Free Hayashi-Miyaura Reaction

A stereodivergent synthesis using inexpensive reagents, i.e., dibenzazepine and glucose-derived t-Bu-sulfinate diastereomers (RS)-6 or (SS)-6, affords respective S(O)-alkene hybrid ligands (S)-7 and (R)-7 on gram scales and in excellent optical purity (ee > 99%). Phenyl substitution of the dibenzoazepine backbone generates planar chirality to give epimerization-resistant (pS,RS)-10 diastereoisomer in high isomeric purity. Furthermore, the crystal structure of widely used sulfinate (RS)-6 is disclosed for the first time since its discovery a quarter of a century ago. Ligands 7 and 10 coordinate Rh(I) in a bidentate fashion through the S atoms and the alkene functions as evidenced by the crystal structures of complexes (R)-11 and (SN,SS)-12. (R)-11 catalyzes the conjugate addition of arylboronic acids to enones with enantioselectivities of up to 77% ee. The reaction proceeds smoothly also under base-free conditions at 40 °C. The planar chirality in ligand (pS,RS)-10 is shown to override and invert the sense of chiral induction predicted by the configuration of the sulfur donor atom.

A New Type of Chiral Cyclic Sulfinamide–Olefin Ligands for Rhodium-Catalyzed Asymmetric Addition

A new type of chiral cyclic sulfinamide–olefin ligands, N-allylic 2,3-dihydro-1,2-benzoisothiazole 1-oxides, with 2,3-dihydro-1,2-benzoisothiazole 1-oxide as a unique chiral skeleton, is developed for the highly enantioselective rhodium-catalyzed asymmetr

Design and synthesis of polymeric chiral bicyclo[3.3.0] diene as reusable ligand for rhodium-catalyzed asymmetric 1,4-addition

A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. With polymeric diene 6b, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. By using polymeric diene, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. Copyright

Design of chiral sulfoxide-olefins as a new class of sulfur-based olefin ligands for asymmetric catalysis

The design and development of a novel class of chiral sulfur-olefin hybrid ligands with high synthetic feasibility are described. These new sulfoxide-olefin ligands showed excellent catalytic activities and enantioselectivities (up to 98% ee) in rhodium-catalyzed asymmetric 1,4-addition reactions of aryl boronic acids to α,β-unsaturated carbonyl compounds.

Simple N-sulfinyl-based chiral sulfur-olefin ligands for rhodium-catalyzed asymmetric 1,4-additions

A variety of N-sulfinyl-based chiral sulfur-olefin ligands has been successfully developed for the first time for rhodium-catalyzed highly efficient and enantioselective 1,4-additions. The ease of synthesis and needless consideration of the carbon chirality makes this novel type of ligands attractive for asymmetric catalysis.

Design of N-sulfinyl homoallylic amines as novel sulfinamide-olefin hybrid ligands for asymmetric catalysis: Application in Rh-catalyzed enantioselective 1,4-additions

Here we show that simple and readily available chiral sulfinamide-olefins can display great catalytic activities and enantioselectivities in rhodium-catalyzed 1,4-addition reactions. This study represent the first example of chiral sulfur-based olefin ligand class for transition metal-catalyzed asymmetric transformation.

Chiral N-tert-butanesulfinyl α,β-unsaturated ketimine: A simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions

One novel type of chiral olefin/sulfinimide hybrid ligands has been developed through a simple one-step condensation of α,β-unsaturated ketones with tert-butanesulfinamide and utilized successfully for rhodium-catalyzed asymmetric conjugated additions to furnish the desired adducts in high yields with excellent ee's.

Chiral bicyclo[3.3.0]octa-2,5-dienes as steering ligands in substrate-dependent rhodium-catalyzed 1,4-addition of arylboronic acids to enones

The synthesis of disubstituted chiral diene ligands (3aR,6aR)- and (3aS,6aS)-10 with a pentalene backbone from the corresponding bicyclo[3.3.0]octa1,4-diones 7 is described. The latter were accessible by enzymatic resolution of the racemic diol rac-5 and