187404-47-3

Upstream product

• 5682-83-7 (E)-2-benzylidenecyclohexanone 
• 108-94-1 cyclohexanone 
• 100-52-7 benzaldehyde 
• 50648-70-9 trans-2-benzylidenecyclohexanol 
• 51557-09-6 (E)-4-(1-naphthyl)but-3-en-2-one 
• 108-22-5 Isopropenyl acetate 
• 66920-76-1 (3E)-4-(naphthalen-1-yl)but-3-en-2-ol 
• 187404-46-2 (R)-2-[1-phenyl-(E)-methylidene]-1-cyclohexyl acetate 

Downstream Products

• 161972-08-3 (1R,2R)-2-phenylmethyl-cyclohexanol 
• 155320-76-6 (2S)-2-methoxycyclohexanone 

Relevant academic research and scientific papers

Ruthenium-catalysed synthesis of chiral exocyclic allylic alcoholsviachemoselective transfer hydrogenation of 2-arylidene cycloalkanones

An exclusive asymmetric reduction of C=O bonds of 2-arylidene four-, five-, six-, and seven-membered cycloalkanones has been studied systematically. The asymmetric transfer hydrogenation was performed using a robust and commercially available chiral diamine-derived ruthenium complex as a catalyst and HCOOH/Et3N as a hydrogen source under mild conditions, giving 51 examples of chiral exocyclic allylic alcohols in up to 96% yield and 99% ee. This method was also applicable to the gram-scale synthesis of the active intermediates of the anti-inflammatory loxoprofen and natural product (?)-goniomitine.

RuPHOX-Ru-Catalyzed Selective Asymmetric Hydrogenation of Exocyclic α,β-Unsaturated Pentanones

A RuPHOX-Ru catalyzed selective asymmetric hydrogenation of exocyclic α,β-unsaturated ketones has been developed, furnishing the corresponding chiral exocyclic allylic alcohols in high yields and with up to >99.5percent ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 10000 S/C) without any loss in reaction activity and enantioselectivity. The resulting hydrogenated products could be easily transformed to several biologically active compounds with high asymmetric performance. The asymmetric protocol provides an efficient methodology for the synthesis of chiral exocyclic allylic alcohols.

Chiral 2-aromatic methylene naphthenic alcohol and asymmetric synthesizing method thereof

The invention relates to chiral 2-aromatic methylene naphthenic alcohol and an asymmetric synthesizing method thereof. A specific structure of the chiral 2-aromatic methylene naphthenic alcohol is shown as II. According to the method, mono-sulfonyl chiral

A Ferrocene-Based NH-Free Phosphine-Oxazoline Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

A new type of ferrocene-based phosphine-oxazoline ligand has been prepared over a few simple steps. An iridium complex of this ligand is air stable and exhibits excellent performance for the asymmetric hydrogenation of simple ketones (up to 98% yield, up to 99% ee, and 20?000 S/C). Exo-α,β-unsaturated cyclic ketones could be regiospecifically hydrogenated to give chiral allylic alcohols with good results. This study indicates that P,N-ligands can also efficiently promote Ir-catalyzed asymmetric hydrogenation without NH-hydrogen-bonding assistance.

Enantioselective reduction of α,β-enones using an oxazaborolidine catalyst generated in situ from a chiral lactam alcohol

The oxazaborolidine catalyst prepared in situ from the chiral lactam alcohol 3 and 4-iodophenoxyborane was found to catalyze the enantioselective reduction of α,β-enones at -40 °C with a high level of enantioselectivity of up to 90% ee.

Highly Enantioselective Hydrogenation of α-Arylmethylene Cycloalkanones Catalyzed by Iridium Complexes of Chiral Spiro Aminophosphine Ligands

The highly efficient asymmetric hydrogenation of α-arylmethylene cycloalkanones catalyzed by Ir-complexes of chiral spiro aminophosphine ligands was developed, providing chiral exo-cyclic allylic alcohols at high yields with excellent enantioselectivities (up to 97% ee) and high turnover numbers (S/C up to 10,000). This new reaction provided an efficient method for the synthesis of the key intermediate of the active form of the anti-inflammatory loxoprofen.

One-pot synthesis and resolution of chiral allylic alcohols

Substituted α,β-unsaturated ketones were selectively reduced to the corresponding allylic alcohols under mild reaction conditions. The allylic alcohols thus obtained were kinetically resolved by lipase catalyzed transesterification in the same pot to affo

Asymmetric reduction of prochiral cycloalkenones. The influence of exocyclic alkene geometry

The asymmetric reduction of a series of prochiral enones of general structure 1 using the Corey oxazaborolidine 2, leading to enantiomerically enriched allylic cycloalkanols 3 is described. The influence of alkene geometry on both the sense (R vs. S) and

Microbially-aided preparation of (S)-2-methoxycyclohexanone key intermediate in the synthesis of Sanfetrinem

(S) 2-Methoxycyclohexanone 1, useful intermediate in the synthesis of Sanfetrinem 2, is obtained from (S) α-benzylidene cyclohexanol 4, derived from the ketone 3 through a short sequence involving as key step yeast reduction of the carbonyl group. The (R) enantiomer of 1 is similarly accessible from the (R) enantiomer of 4 obtained either upon Candida lipolytica-mediated reduction of 3 or from (R,S)-4 by porcine pancreatic lipase catalyzed acetylation with vinyl acetate. Also the saturated carbinols 7 and 8, which accompany 4 in the microbial reduction of 3, are converted into 1 through unexceptional steps. Nocardia opaca, Pichia etchelsii and Mucor subtilissimus provide from 3 upon reduction (S)-configurated 4, 7 and 8 possessing moderate-high ee values.

Oxazaborolidine-mediated reduction of prochiral 2-alkylidene cycloalkanones

Asymmetric reduction of enones 1a-g using either a stoichiometric or catalytic amount of oxazaborolidine 3 proceeds to give the synthetically useful allylic cycloalkanols 2a-g in 83-96% e.e.