One-pot synthesis of lactams using domino reactions: combination of Schmidt reaction with Sakurai and aldol reactions.
A series of domino reactions in which the intramolecular Schmidt reaction is combined with either a Sakurai reaction, an aldol reaction, or both is reported. The Sakurai reaction of an allylsilane with an azido-containing enone under Lewis acidic conditions followed by protonation of the resulting titanium enolate species allowed for a subsequent intramolecular Schmidt reaction. Alternatively, the intermediate titanium enolate could undergo an aldol reaction followed by the intramolecular Schmidt reaction to form lactam products with multiple stereogenic centers. The stereochemical features of the titanium enolate aldol reaction with several 3-azidoaldehyde substrates during this domino process is discussed.
Huh
Chan Woo
CW
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, University of Kansas, Lawrence, Kansas 66045-7582, USA.
Somal
Gagandeep K
GK
Katz
Christopher E
CE
Pei
Huaxing
H
Zeng
Yibin
Y
Douglas
Justin T
JT
Aubé
Jeffrey
J
D000447:Aldehydes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000447:Aldehydes; D000900:Anti-Bacterial Agents; D007769:Lactams; C116609:3-hydroxybutanal