97023-56-8

Upstream product

• 109-72-8 n-butyllithium 
• 637-44-5 phenylpropyolic acid 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 1009-14-9 phenyl butyl ketone 

Downstream Products

• 5638-30-2 acide 3-phenyl-heptanoique 

Relevant academic research and scientific papers

Construction of C-S bonds with a quaternary stereocenter through a formal Michael reaction: Asymmetric synthesis of tertiary thiols

Quaternary stereocenters that bear a sulfur substituent can be created with nearly perfect stereocontrol through an intramolecular Michael-type process. Lewis acids (L.A.) accelerate the intramolecular sulfur-atom transfer from the oxazolidine-2-thione functionality to the β carbon atom of the β,β-disubstituted enoyl moiety, whereas the chirality of the oxazolidine-2-thione portion controls reaction stereochemistry (see scheme).

Photocatalytic E → Z isomerization of polarized alkenes inspired by the visual cycle: Mechanistic dichotomy and origin of selectivity

Iteratively executed with exquisite spatial and temporal control, the selective isomerization of polarized alkenes underpins a plethora of complex biological processes ranging from natural product biosynthesis through to the mammalian visual cycle. However, nature's proficiency conceals the inherent difficulties in replicating this contrathermodynamic transformation in the laboratory. Recently, we disclosed the first highly Z-selective isomerization of polarized alkenes, employing the cinnamoyl chromophore as a retinal surrogate under UV-irradiation (402 nm) with (-)-riboflavin (Vitamin B2) as an inexpensive, organic photocatalyst (J. Am. Chem. Soc. 2015, 137, 11254-11257). This study was inspired by the propensity of crystalline (-)-riboflavin in the eyes of vertebrates to invert the intrinsic directionality of retinal isomerization. Herein, we extend this methodology to include a bioinspired, catalytic E → Z isomerization of α,β-unsaturated nitriles, thereby mimicking the intermediate Opsin-derived, protonated Schiff base in the visual cycle with simple polarized alkenes. Replacement of the iminium motif by a cyano group is well tolerated and gives an additional degree of versatility for postisomerization functionalization. Broad substrate scope is demonstrated (up to 99:1 Z:E) together with evidence of mechanistic dichotomy via both singlet and triplet energy transfer mechanisms. Kinetic studies, temperature dependent photostationary state correlations and investigation of substituent-based electronic perturbation of the alkene identified polarization combined with increased Z-isomer activation barriers as the selectivity governing factors in catalysis. This investigation demonstrates the importance of internal structural preorganization on photostationary composition and explicates the augmented Z-selectivity upon hydrogen-alkyl exchange at the β-position of the alkene.

BICYCLIC 1,3,4-OXADIAZOLE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTORS' MODULATORS

The present invention relates to bicyclic 1,3,4-oxadiazole derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of sphingosine-1-phosphate receptors.

1,3,4-ALKENYL OXADIAZOLE AMINO ACID DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTORS' MODULATORS

The present invention relates to 1,3,4-alkenyl oxadiazole amino acid derivatives of formulae I and II, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of sphingosine-1-phosphate receptors.

Contrasting behaviour of (E)-3-(trimethylsilyl)- and (E)-3-phenylpropenoic acids towards n-butyl- and tert-butyllithium

The title compounds 2 and 9 react with tert-buthyllithium to give considerable amounts of 'anti-Michael' adducts 3 and 10, respectively, in which the tert-butyl group is bonded to C-2.A single-electron-transfer (SET) mechanism is proposed for these reacti