Journal
ORGANIC LETTERS
Volume 10, Issue 11, Pages 2223-2226Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol800649n
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Funding
- NIGMS NIH HHS [P50 GM069663, P50 GM069663-030001] Funding Source: Medline
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An asymmetric approach for the synthesis of substituted delta-sultams with multiple synthetic handles is described. This study demonstrates the facile construction of a stereochemically diverse array of substituted delta-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 delta-sultams in good yields.
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