942416-33-3

Upstream product

• 36805-43-3 ethyl (E)-3-methyl-5-phenylpent-2-enoate 
• 72681-02-8 (Z)-3-Methyl-5-phenyl-2-penten-1-ol 
• 72681-08-4 (E)-3-methyl-5-phenyl-pent-2-en-1-ol 
• 3277-89-2 phenethylmagnesium bromide 
• 123-73-9 crotonaldehyde 
• 33046-84-3 (2E)-5-phenyl-2-pentenal 
• 75-16-1 methylmagnesium bromide 
• 37868-70-5 5-phenyl-pent-2-enal 
• 544-97-8 dimethyl zinc(II) 
• 26429-97-0 methyl (2E)-5-phenyl-2-pentenoate 
• 103766-22-9 2-(3-phenylpropylidene)malonic acid diethyl ester 
• 55053-55-9 (+)-(R)-ethyl 3-methyl-5-phenylpentanoate 

Relevant academic research and scientific papers

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.

Stereoselective Synthesis of Baulamycin A

New structural classes of antibiotics are rare, structurally novel broad-spectrum antibiotics exceptionally so. The recently discovered baulamycins constitute a remarkable example of these highly prized compounds and, as such, have attracted considerable attention in the form of both synthetic efforts and biological studies. For the first time, we report a gram-scale preparation of the common carbon framework of the baulamycin family, as well as the total synthesis of its most potent member, baulamycin A. Our approach employs highly stereoselective, catalyst-controlled asymmetric conjugate additions to thioesters to set key stereocenters, as well as the first reported use of "dry ozonolysis" to reveal a masked carboxylic acid in the total synthesis of a natural product.

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C-C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

Asymmetric addition of dimethylzinc to alkylidenmalonates mediated by phosphorous ligands: A new synthetic route to floral fragrances

Six new phosphite ligands were prepared and their efficiency as chiral ligands was investigated in the copper-catalyzed asymmetric conjugate addition of dimethylzinc to diethyl 3-phenylpropylidenmalonate (5), affording the addition product with ees up to 74%. Moreover, a simple and straightforward route to floral fragrances Phenoxanol, Citralis, and Nitrile Citralis in optically active form through the above cited reaction was proposed. Chirality, 2011. 2011 Wiley-Liss, Inc. Copyright

Copper-catalyzed enantioselective 1,4-addition to α,β- unsaturated aldehydes

Figure presented The first asymmetric Cu-catalyzed conjugate addition of dialkylzinc zinc reagents to a large scope of enals in presence of phosphoramidite, SimplePhos, or (R)-BINAP ligands with enantiomeric excesses up to 90% is reported. Moreover, ACA of Grignard reagents afforded moderate to good 1,4-regioselectivities with enantioselectivities up to 90%.

Asymmetric catalysis in fragrance chemistry: a new synthetic approach to enantiopure Phenoxanol, Citralis and Citralis Nitrile

A new approach to the synthesis of the single stereomers of the fragrances Phenoxanol, Citralis and Citralis Nitrile is reported. The key step of the synthesis is the asymmetric hydrogenation of (Z)- or (E)-3-methyl-5-phen