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An RCM strategy to stereodiverse delta-sultam scaffolds.

ABSTRACT: 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.

SUBMITTER: Jimenez-Hopkins M

PROVIDER: S-EPMC2641035 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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An RCM strategy to stereodiverse delta-sultam scaffolds.

Jiménez-Hopkins María M Hanson Paul R PR

Organic letters 20080501 11

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 diaste ...[more]

PMID: 18447383

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