1
2006 Oxazine derivatives R 0595 Synthesis of 7,8-Benzo-9-aza-4-oxabicyclo[3.3.1]nonan-3-ones by Sequential "Condensation—Iodolactonization" Reactions of 1,1-Bis(trimethylsilyl- oxy)ketene Acetals with Isoquinolines. — Condensation of isoquinolines with meth- yl chloroformate and 1,1-bis(silyloxy)ketene acetals and subsequent iodolactonization give 9-aza-4-oxabicyclo[3.3.1]nonan-3-ones regio- and diastereospecifically. — (ULLAH, E.; ROTZOLL, S.; SCHMIDT, A.; MICHALIK, D.; LANGER*, P.; Tetrahedron Lett. 46 (2005) 52, 8997-8999; Leibniz-Inst. Org. Katal., Univ. Rostock, D-18055 Rostock, Germany; Eng.) — Mais 14- 168

Synthesis of 7,8-Benzo-9-aza-4-oxabicyclo[3.3.1]nonan-3-ones by Sequential “Condensation—Iodolactonization” Reactions of 1,1-Bis(trimethylsilyloxy)ketene Acetals with Isoquinolines

Embed Size (px)

Citation preview

2006

Oxazine derivativesR 0595 Synthesis of 7,8-Benzo-9-aza-4-oxabicyclo[3.3.1]nonan-3-ones by Sequential

"Condensation—Iodolactonization" Reactions of 1,1-Bis(trimethylsilyl-oxy)ketene Acetals with Isoquinolines. — Condensation of isoquinolines with meth-yl chloroformate and 1,1-bis(silyloxy)ketene acetals and subsequent iodolactonization give 9-aza-4-oxabicyclo[3.3.1]nonan-3-ones regio- and diastereospecifically. — (ULLAH, E.; ROTZOLL, S.; SCHMIDT, A.; MICHALIK, D.; LANGER*, P.; Tetrahedron Lett. 46 (2005) 52, 8997-8999; Leibniz-Inst. Org. Katal., Univ. Rostock, D-18055 Rostock, Germany; Eng.) — Mais

14- 168