Title of article
Highly diastereoselective synthesis of bicyclo[4.2.0]octanone derivatives by the [2+2] photocycloaddition of chiral cyclohexenonecarboxylates to ethylene
Author/Authors
Furutani، نويسنده , , Akinori and Tsutsumi، نويسنده , , Ken and Nakano، نويسنده , , Hiroaki and Morimoto، نويسنده , , Tsumoru and Kakiuchi، نويسنده , , Kiyomi، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2004
Pages
4
From page
7621
To page
7624
Abstract
The diastereoselective [2+2] photocycloaddition of a cyclohexenonecarboxylate containing (−)-8-(4-nitrophenyl)menthyl as a chiral auxiliary to ethylene gave the photocycloadduct, a bicyclo[4.2.0]octanone derivative, with a high degree of diastereoselectivity. A photoreaction, conducted in CH2Cl2 at −78 °C gave the corresponding photocycloadduct in 88% de. In the presence of Ti(OR)4 or Me3SnCl, the diastereoselectivity was increased up to 92% de.
Keywords
Cyclohexenone , chiral auxiliary , Menthyl , Lewis acid , diastereoselectivity
Journal title
Tetrahedron Letters
Serial Year
2004
Journal title
Tetrahedron Letters
Record number
1843475
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