Use of N-allylidene-1,1-diphenylethanamine as a latent acrolein synthon in the double nucleophilic addition reaction of ketene silyl (Thio)acetals and allylborolanes.
In the presence of silica gel and water, a mixture of ketene silyl acetals and 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane underwent 1,4- and subsequently 1,2-addition with N-allylidene-1,1-diphenylethanamine to give delta-hydroxyesters in good yields, where the allylideneamine was successfully used as an acrolein equivalent.
Shimizu
Makoto
M
Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan. mshimizu@chem.mie-u.ac.jp
Kawanishi
Mami
M
Mizota
Isao
I
Hachiya
Iwao
I
D000080:Acetals / Q000737:chemistry*; D000171:Acrolein / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D015394:Molecular Structure; D010627:Phenethylamines / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000080:Acetals; D000814:Aniline Compounds; D001896:Boron Compounds; D004952:Esters; C553377:N-allylidene-1,1-diphenylethanamine; D010627:Phenethylamines; D012821:Silanes; D000171:Acrolein