40564-16-7

Upstream product

• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 124-13-0 Octanal 
• 120-92-3 cyclopentanone 

Downstream Products

• 40566-23-2 2-octyl-cyclopentanone 

Relevant academic research and scientific papers

ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS

The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo--selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R", NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R" are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R" form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R" are attached; and wherein said compound is free from a metal catalyst.

A novel pyrrolidine imide catalyzed direct formation of α,β-unsaturated ketones from unmodified ketones and aldehydes

(Chemical Equation Presented) A method for direct, stereoselective preparation of (E)-α,β-unsaturated ketones from ketones and aldehydes, promoted by a novel pyrrolidine imide organocatalyst, has been developed in moderate to high yields. Unlike the Claisen-Schmidt condensation and Lewis acid catalyzed tandem aldol-dehydration processes, this method provides mild reaction conditions to access α,β-unsaturated ketones from simple, unmodified ketones.

Cross-Condensation Reactions of Cycloalkanones with Aldehydes and Primary Alcohols under the Influence of Zirconocene Complexes.

Under the influence of zirconocene complex,Cp2ZrH2 (1) or Cp2Zr(O-i-Pr)2 (9),cycloalkanones 2 condensed directly with aliphatic aldehydes 3 or primary alcohols 7 to form 2-alkylidenecycloalkanones 4 or 2-alkyl-2-cycloalken-1-ones 8,respectively,in fair to substantial yields.The selectivity of the cross-condensations was slighty improved by using 1 in combination with a metal salt such as NiCl2.Dihydrojasmone (13) was synthesized in 35percent yield by one-step reaction from the commercially available 3-methylpentanone (2e) with pentanol (7b) in the presence of 1 and NiCl2.