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Synfacts 2010(11): 1292-1292
DOI: 10.1055/s-0030-1258722
DOI: 10.1055/s-0030-1258722
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New YorkN-Allylidene-1,1-diphenylethanamine as Acrolein Synthon
Contributor(s):Paul Knochel, Thomas KunzM. Shimizu*, M. Kawanishi, I. Mizota, I. Hachiya
Mie University, Tsu, Japan
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
Org. Lett. 2010, 12: 3571-3573
Mie University, Tsu, Japan
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
Org. Lett. 2010, 12: 3571-3573
Further Information
Publication History
Publication Date:
21 October 2010 (online)
Key words
silica - 1,2-addition - acrolein synthons
Significance
A synthetic pathway leading to δ-hydroxy esters in good yields is reported. N-Allylidene-1,1-diphenylethanamine is used as an acrolein equivalent which reacted with ketene silyl acetals and 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in subsequent 1,4- and 1,2-double nucleophilic additions.
Comment
The best results were obtained by initially mixing all reagents in methylene chloride at -78 ˚C and adding water after 1.5 hours. The diastereoselectivities are not always high.