Synthesis of azoxabicyclo[3.3.1]nonanones based on diastereoselective reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines and quinolines.
Densely functionalized azoxabicyclo[3.3.1]nonanones were prepared by regio- and diastereoselective condensation of 1,1-bis(silyloxy)ketene acetals with isoquinolinium and quinolinium salts and subsequent regioselective and stereospecific iodolactonization.
Schmidt
Andreas
A
Institut für Chemie, Universität Rostock, Rostock, Germany.
Michalik
Dirk
D
Rotzoll
Sven
S
Ullah
Ehsan
E
Fischer
Christine
C
Reinke
Helmut
H
Görls
Helmar
H
Langer
Peter
P
D000080:Acetals / Q000737:chemistry*; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry; D005561:Formates / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000080:Acetals; D053961:Azabicyclo Compounds; D005030:Ethylenes; D005561:Formates; D007546:Isoquinolines; D007659:Ketones; D011804:Quinolines; D014297:Trimethylsilyl Compounds; C008223:ketene; C014667:methyl chloroformate