132559-69-4

Upstream product

• 132559-60-5 5-[1,2,4]Trioxolan-3-yl-pentan-2-one 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 21856-89-3 6-hydroxy-2-hexanone 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 21889-88-3 hept-6-en-2-one 
• 6048-29-9 triphenylphenacylphosphonium bromide 
• 70-11-1 α-bromoacetophenone 
• 505-03-3 5-oxohexanal 
• 693-89-0 1-methylcyclopent-1-ene 

Downstream Products

• 1241735-13-6 cis-(2-hydroxy-2-methylcyclohexyl)phenylmethanone 
• 137204-79-6 2-((1R,2S)-2-Hydroxy-2-methyl-cyclopentyl)-1-phenyl-ethanone 

Relevant academic research and scientific papers

Enantioselective Synthesis of Spiro-oxiranes: An Asymmetric Addition/Aldol/Spirocyclization Domino Cascade

Enantioenriched spiro-oxiranes bearing three contiguous stereocenters were synthesized using a rhodium-catalyzed asymmetric addition/aldol/spirocyclization sequence. Starting from a linear substrate, the cascade enabled the formation of a spirocyclic framework in a single step. sp2- and sp-hybridized carbon nucleophiles were found to be competent initiators for this cascade, giving arylated or alkynylated products, respectively. Derivatization studies demonstrated the synthetic versatility of both the epoxide and the alkyne moieties of the products. DFT calculations were used to reconcile spectroscopic discrepancies observed between the solution- and solid-state structures of the products.

Rhodium-Catalyzed Asymmetric Conjugate Alkynylation/Aldol Cyclization Cascade for the Formation of α-Propargyl-β-hydroxyketones

A rhodium-catalyzed conjugate alkynylation/aldol cyclization cascade was developed. Densely functionalized cyclic α-propargyl-β-hydroxyketones were synthesized with simultaneous formation of a C(sp)-C(sp3) bond, a C(sp3)-C(sp3) bond, as well as three new contiguous stereocenters. The transformation was achieved with excellent enantio- and diastereoselectivities using BINAP as the ligand. The synthetic utility of the newly installed alkynyl moiety was exhibited by subjecting the products to an array of derivatizations.

Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds

The expanding “toolbox” of biocatalysts opens new opportunities to redesign synthetic strategies to target molecules by incorporating a key enzymatic step into the synthesis. Herein, we describe a general biocatalytic approach for the enantioselective preparation of 2,6-disubstituted piperidines starting from easily accessible pro-chiral ketoenones. The strategy represents a new biocatalytic disconnection, which relies on an ω-TA-mediated aza-Michael reaction. Significantly, we show that the reversible enzymatic process can power the shuttling of amine functionality across a molecular framework, providing access to the desired aza-Michael products.

Syntheses of α,β-unsaturated carbonyl compounds from the reactions of monosubstituted ozonides with stable phosphonium ylides

Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-αβ-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-αβ-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position of the heteroatom in the substituent of the ozonides. The possible mechanism of this reaction will be discussed. (C) 2000 Elsevier Science Ltd.

The Reaction of Ozonides from Mono-substituted Alkenes with Stabilized Phosphorus Ylides

Ozonides derived from mono-substituted alkenes react with methyl (triphenylphosphoranylidene)acetate or (triphenylphosphoranylidene)acetophenone to form trans-α,β-unsaturated esters or ketones, respectively, in high yields.