Total synthesis of sedum alkaloids via catalyst controlled aza-cope rearrangement and hydroformylation with formaldehyde
The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn-and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.
Ren, Hong,Wulff, William D.
supporting information
p. 242 - 245
(2013/03/28)
Hydroformylation of alkenylamines. Concise approaches toward piperidines, quinolizidines, and related alkaloids
Linear hydroformylation of N-protected allyl- or homoallylamines (cyclohydrocarbonylation: CHC), followed by a reductive amination constitute the two key steps toward convenient routes to aza-heterocycles.
Airiau, Etienne,Girard, Nicolas,Pizzeti, Marianna,Salvadori, Jessica,Taddei, Maurizio,Mann, Andre
supporting information; experimental part
p. 8670 - 8673
(2011/02/28)
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