Synthesis of azoxabicyclo[3.3.1]nonanones based on diastereoselective reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines and quinolines

Andreas Schmidt; Dirk Michalik; Sven Rotzoll; Ehsan Ullah; Christine Fischer; Helmut Reinke; Helmar Görls; Peter Langer

doi:10.1039/b804139c

Synthesis of azoxabicyclo[3.3.1]nonanones based on diastereoselective reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines and quinolines

Org Biomol Chem. 2008 Aug 7;6(15):2804-14. doi: 10.1039/b804139c. Epub 2008 Jun 12.

Authors

Andreas Schmidt¹, Dirk Michalik, Sven Rotzoll, Ehsan Ullah, Christine Fischer, Helmut Reinke, Helmar Görls, Peter Langer

Affiliation

¹ Institut für Chemie, Universität Rostock, Rostock, Germany.

PMID: 18633539
DOI: 10.1039/b804139c

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetals / chemistry*
Azabicyclo Compounds / chemical synthesis*
Azabicyclo Compounds / chemistry
Cyclization
Ethylenes / chemistry
Formates / chemistry
Isoquinolines / chemistry*
Ketones / chemistry
Molecular Structure
Quinolines / chemistry*
Stereoisomerism
Trimethylsilyl Compounds / chemistry*

Substances

Acetals
Azabicyclo Compounds
Ethylenes
Formates
Isoquinolines
Ketones
Quinolines
Trimethylsilyl Compounds
ketene
methyl chloroformate