3626-97-9Relevant articles and documents
Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin
Barma, Deb K.,Lu, Biao,Baati, Rachid,Mioskowski, Charles,Falck
, p. 4359 - 4361 (2008/12/21)
The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.
A new synthetic approach to α-chlorocinnamaldehydes
Nenajdenko, Valentine G.,Reznichenko, Alexander L.,Lenkova, Olesya N.,Shastin, Alexey V.,Balenkova, Elizabeth S.
, p. 605 - 609 (2007/10/03)
A new simple and efficient transformation of aromatic aldehydes into α-chlorocinnamaldehydes is described. Catalytic olefination reaction of hydrazones of aromatic aldehydes with 2-trichloromethyl-1,3-dioxolane gives ethylene acetals of target alkenes in moderate to good yields. The reaction proceeds stereoselectively to form preferably Z-isomers.
