A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N‐Boc‐Protected Imines

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公開日
2009-02-17
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.200805628
  • 10.1002/ange.200805628
  • 10.1002/chin.200925030
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p><jats:bold>The moderate nucleophilicity</jats:bold> of the axially chiral amino sulfonamide (<jats:italic>S</jats:italic>)‐<jats:bold>1</jats:bold> suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N‐Boc‐protected imines with aldehydes. The corresponding adducts are obtained in good yield and excellent stereoselectivity (see scheme; Boc=<jats:italic>tert</jats:italic>‐butoxycarbonyl, Tf=trifluoromethanesulfonyl).<jats:boxed-text content-type="graphic" position="anchor"><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/gif" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/mcontent.gif"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text></jats:p>

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