253197-70-5

Upstream product

• 2160-89-6 1,1,1,3,3,3-hexafluoroisopropyl acrylate 
• 100-52-7 benzaldehyde 

Downstream Products

• 36041-80-2 (2R,3S)-methyl 3-hydroxy-2-methyl-3-phenylpropanoate 

Relevant academic research and scientific papers

Stereoselective Construction of Entire Diastereomeric Stereotetrads Based on an Asymmetric Morita–Baylis–Hillman Reaction

A method for the enantio- and diastereoselective construction of all possible stereoisomers of a polypropionate stereotetrad having four contiguous stereogenic centers has been developed. The approach features an iterative sequence of cinchona-alkaloid-ca

Synthesis of a pseudoenantiomer of β-isocupreidine (β-ICD), a chiral amine catalyst for asymmetric baylis-hillman reactions

-(3S,8S,9R)-3,9-Epoxy-6′-hydroxy-11-norcinconane (23), a pseudoenantiomer of β-isocupreidine (β-ICD), was synthesized starting with a fragmentation reaction of 10-bromo-10,11-dihydroquinine, prepared from quinine. Baylis-Hillman reaction of benzaldehyde w

α-isocupreine, an enantiocomplementary catalyst of β-isocupreidine

Complementary chemistry! α-Isocupreine (α-ICPN) was synthesized for the first time in one step from quinine by treatment with CF 3SO3H (see scheme). This compound serves as an enantiocomplementary catalyst to β-isocupreidine (β-ICD)

A bifunctional β-isocupreidine derivative as catalyst for the enantioselective morita-baylis-hillman reaction and a mechanistic rationale for enantioselectivity

Starting from β-isocupreidine (β-ICD), a series of difunctional catalysts were synthesized to ascertain their usefulness in the asymmetric Morita-Baylis-Hillman (MBH) reaction. The trichloroacetylcarbamate derivative was found to give the (R)-MBH adducts in excellent optical purities (90-99% ee) and moderate to good yields (43-83%), in some cases, better than β-ICD. A number of acrylates were also tested and 2,6-dimethyl-4-nitrophenyl acrylate was identified as a suitable alternative to the popular hexafluoroisopropyl acrylate, with both the β-ICD and trichloroacetylcarbamate derivatives. The mechanism of the rate- and selectivity-determining step was ascertained by means of experimental observations and a computational investigation aimed at clarifying the transition state structures is reported. These studies have clarified the reasons for the effectiveness of these structurally related catalysts in the asymmetric MBH reaction between acrylates and aldehydes. β-Isocupreidine derivatives were used tocatalyze the asymmetric Morita-Baylis-Hillman (MBH) reaction, giving the (R)-MBH adducts in excellent optical purities and moderate to good yields. Both 2,6-dimethyl-4-nitrophenyl and hexafluoroisopropyl acrylate could be used. The rate- and selectivity-determining step was identified and the structures of the preferred transition states were computed.

Synthesis of an enantiocomplementary catalyst of β-isocupreidine (β-ICD) from quinine

Compound 20, a pseudoenantiomer of β-isocupreidine (β-ICD), was synthesized from quinine employing a Barton reaction of nitrosyl ester 13 and acid-catalyzed cyclization of carbinol 18 as key steps. The Baylis-Hillman reaction of benzaldehyde, p-nitrobenza