Asymmetric aza-Michael addition under ultra-high pressure: short bias to polyhydroxylated piperidines

作者:Moura Sidnei*; Thomassigny Christine; Ligeour Caroline; Greck Christine; Joseph Delphine; Drege Emmanuelle; Dumas Francoise
来源:Green Chemistry, 2011, 13(7): 1812-1818.
DOI:10.1039/c1gc15097a

摘要

Two polyhydroxylated piperidines have been prepared in short sequences from diacetone gluco- and allofuranose. The key step is a piezo-aza-Michael addition of diphenylmethanamine to enoates bearing a sugar moiety in the gamma-position. The combination of ultra-high pressure associated to the presence of readily available sugars chiral pool led to the expected chiral amines in good yields and excellent stereoselectivities.

  • 出版日期2011