652160-84-4Relevant academic research and scientific papers
Catalytic enantioselective conjugate addition of dialkyl zinc reagents to α,β-unsaturated ketones mediated by new phosphite ligands containing binaphthalene/1,2-diphenylethane moieties: A practical synthesis of (R)-(-)-muscone
Scafato, Patrizia,Labano, Stefania,Cunsolo, Giovanni,Rosini, Carlo
, p. 3873 - 3877 (2003)
New diastereoisomeric phosphites based on either (R)- or (S)-2,2′-dihydroxy-1,1′-binaphthyl (BINOL) and having the chiral alcoholic moiety derived from the monobenzyl ether of (R,R)-1,2-diphenylethane- 1,2-diol have been prepared and used as chiral ligands in the enantioselective copper-catalyzed 1,4-addition of diethylzinc to chalcone and 2-cyclohexen-1-one (enantiomeric excesses up to 48%). With the (aR,R,R) ligand dimethylzinc adds enantioselectively to (E)-cyclopentadecen-2-en-1-one to give (R)-(-)-muscone (68% yield, 78% ee). This provides an efficient access to a valuable ingredient of the perfume industry. However, with the (aS,R,R) ligand, (S)-(+)-muscone is obtained with longer reaction times (37% yield and 10% ee) with a very high double diastereoselection effect being observed.
Asymmetric addition of dimethylzinc to alkylidenmalonates mediated by phosphorous ligands: A new synthetic route to floral fragrances
Superchi, Stefano,Marchitiello, Valeria,Pisani, Laura,Scafato, Patrizia
experimental part, p. 761 - 767 (2012/01/13)
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
