An RCM Strategy to Stereodiverse δ-Sultam Scaffolds
- 1 May 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (11), 2223-2226
- https://doi.org/10.1021/ol800649n
Abstract
An asymmetric approach for the synthesis of substituted δ-sultams with multiple synthetic handles is described. This study demonstrates the facile construction of a stereochemically diverse array of substituted δ-sultams, more specifically substituted 3,4,5,6-dihydro 1,2-thiazine 1,1-dioxides. A pivotal Mitsunobu alkylation/RCM sequence is used to assemble key allyl sultam building blocks possessing a C3 stereogenic handle. All subsequent reactions are achieved with high levels of diastereoselectivity to afford enantiopure δ-sultams in good yields.Keywords
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