Title of article
Asymmetric cycloetherification based on a chiral auxiliary for 4-acyloxy-1-butene substrates during oxidation with iodosylbenzene via a 1,3-dioxan-2-yl cation
Author/Authors
Fujita، نويسنده , , Morifumi and Ookubo، نويسنده , , Yuuya and Sugimura، نويسنده , , Takashi، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2009
Pages
3
From page
1298
To page
1300
Abstract
Reaction of but-3-enyl camphanate and its derivatives with iodosylbenzene yielded tetrahydrofuran-3-yl camphanate with high diastereomeric ratio via a 1,3-dioxan-2-yl cation intermediate. The reaction using (1S)-camphanate as a chiral auxiliary preferentially gave (S)-3-acyloxytetrahydrofuran and (2S,3S)-3-acyloxy-2-silyltetrahydrofuran.
Keywords
Neighboring group participation , Iodosylbenzene , Tetrahydrofuran , hypervalent iodine , chiral auxiliary
Journal title
Tetrahedron Letters
Serial Year
2009
Journal title
Tetrahedron Letters
Record number
1862906
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