Title of article
Serendipitous synthesis of a ditwistane: a one-step access!
Author/Authors
Gabriele Berkenbusch، نويسنده , , Thilo and Laungani، نويسنده , , Andy Ch. and Brückner، نويسنده , , Reinhard and Keller، نويسنده , , Manfred، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2004
Pages
4
From page
9517
To page
9520
Abstract
4-tert-Butyl-2-cyclohexen-1-one dimerizes in THF solution via its kinetic enolate, leading to di-tert-butylditwistane 8 in up to 36% yield (−78 °C → room temp., protonolysis, flash chromatography). X-ray crystallography shows that 8 incorporates one R and one S enantiomer of the starting ketone; none of the diastereomeric ditwistanes epi-8, epi’-8 or iso-8 was isolated. This means that the formation of 8 proceeds with mutual kinetic resolution and 100% induced diastereoselectivity.
Keywords
Twistane , Polycyclic hydrocarbon , Tandem reaction
Journal title
Tetrahedron Letters
Serial Year
2004
Journal title
Tetrahedron Letters
Record number
1844246
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