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1999
ring closure reactions
ring closure reactions
O 0130
Radical Cyclization in Heterocycle Synthesis. Part 6. A New Entry
32 - 042 to Cyclic Amino Alcohols via Stannyl Radical Cyclization of Oxime
Ethers Connected with Aldehydes or Ketones.
— Five- to sevenmembered heterocycles functionalized adjacently with amino and hydroxyl
groups are prepared by intramolecular cyclization of oxime ethers, tethered via
a nitrogen atom to aldehyde or ketone groups, in the presence of Bu3 SnH and
AIBN. In all cases the trans isomers are the major products. The attempted
formation of eight-membered products (Vc)/(VIc) fails and the starting compound (IVc) is mostly recovered.
— (NAITO, TAKEAKI; NAKAGAWA,
KAZUMI; NAKAMURA, TAKAKO; KASEI, AKIRA; NINOMIYA, ICHIYA;
KIGUCHI, TOSHIKO; J. Org. Chem. 64 (1999) 6, 2003-2009; Kobe Pharm.
Univ., Higashinada, Kobe 658, Japan; EN)
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