250281-46-0

Upstream product

• 55846-67-8 1,3-Dicyclohexyl-1,3-propanedione 
• 77291-92-0 (R,R)-1,3-diphenyl-1,3-propanediol 

Downstream Products

• 250281-50-6 (S,S)-1,3-dicyclohexyl-1,3-propanediazide 
• 250281-51-7 (S,S)-1,3-dicyclohexyl-1,3-propanediamine 

Relevant academic research and scientific papers

Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence

An established route to enantiomerically pure β-hydroxy ketones proceeds through the asymmetric hydrogenation of β-keto esters, an ester/amide exchange, and the use of the resulting β-hydroxy amide for the acylation of an organometallic compound. We shortened this route by showing that β-keto Weinreb amides are hydrogenated with up to 99 % ee in the presence of [Me2NH2]+{[RuCl(S)-BINAP]2(μ-Cl)3}–(0.5 mol-%) at room temp./5 bar. These Weinreb amides were prepared by seemingly obvious yet unprecedented condensations of lithiated N-methoxy-N-methylacetamide with carboxylic chlorides (51–87 % yield). The resulting β-hydroxy Weinreb amides were used for the acylation of organolithium and Grignard reagents. They thus gave enantiomerically pure β-hydroxy ketones (28 examples). A selection of these compounds gave anti-1,3-diols after another C=O bond hydrogenation, or syn-1,3-diols by a Narasaka–Prasad reduction.

Synthesis of the C2-symmetric 1,3-dicyclohexyl-1,3-propanediol and diamine enantiomers

The parent C2-symmetric (R,R)- and (S,S)-1,3-dicyclohexyl-1,3- propanediols and diamines are readily obtained from the corresponding diphenyldiol precursors.

Chiral 1,2-bis(phosphetano)benzenes: Preparation and use in the Ru- catalyzed hydrogenations of carbonyl derivatives

Chiral 1,2-bis(phosphetano)benzenes are readily prepared from accessible, optically pure 1,3-diol cyclic sulfates. Their ruthenium complexes catalyze the enantioselective hydrogenations of functionalized carbonyls with moderate-to-high enantiomeric excesses. High levels of diastereo- and enantioselectivity are achieved, especially in the hydrogenation of β-diketones to the corresponding anti-1,3-diols.

Enantioselective synthesis ofanti 1, 3-diols via ru(ii)-catalyzed hydrogénations

The homogeneous ruthenium-catalyzed hydrogénation of new symmetrical 1, 3-diketones has been achieved with various ligands including SKEWPHOS and Me-DuPHOS. Complete conversions with enantiomeric and diastereomeric excesses up to 99% were obtained. This represents a new catalytic application of the chiral ligands above. Thieme Stuttgart.