An Ethynyl-Substituted 1,5,7-Trimethyl-3-azabicyclo[3.3.1]nonan-2-one as a Versatile Precursor for Chiral Templates and Chiral Photocatalysts

作者：Voss Felix; Bach Thorsten^*

来源：Synlett, 2010, 2010(10): 1493-1496.

DOI：10.1055/s-0029-1219920

• cycloadditions
• cyclobutanes
• enantioselectivity
• heterocycles
• organocatalysis
• photochemistry

The title compound was synthesized and separated into its enantiomers. The enantiomerically pure alkyne was ligated to several aryl azides and aryl halides. The resulting 7-substituted 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-ones were used either as chiral templates in the intramolecular [2+2] photocycloaddition of 4-allyloxyquinolone (up to 72% ee) or as a chiral photocatalyst for the intramolecular [2+2] photocycloaddition of 4-(3-butenyloxy)quinolone (up to 79% ee with 10 mol% catalyst).

• 出版日期2010-6