1,1′‐Binaphthyldiamine‐Based Lewis Bases as Readily Available and Efficient Organocatalysts for the Reduction of <i>N</i>‐Aryl and <i>N</i>‐Alkyl Ketimines
書誌事項
- 公開日
- 2009-07-14
- 権利情報
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- http://onlinelibrary.wiley.com/termsAndConditions#vor
- DOI
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- 10.1002/ejoc.200900524
- 公開者
- Wiley
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説明
<jats:title>Abstract</jats:title><jats:p>The development of simple, low‐cost, efficient, and sustainable routes to enantiomerically pure amines is a topic of extraordinary interest, specially in view of future industrial applications. In this context, we wish to report a chemical and stereochemical efficient synthesis of chiral amines through the Lewis base activated trichlorosilane reduction of ketimines. An organocatalyst, easily prepared in a single step through the condensation of picolinic acid and commercially available 1,1′‐binaphthyldiamine, is the key element of this metal‐free methodology, that allowed the synthesis of chiral secondary and primary amines in high yields and stereoselectivity. Noteworthy, such catalysts are able to promote the reduction of <jats:italic>N</jats:italic>‐alkyl ketimines, often in quantitative yield and up to 87 % enantioselectivity; it is worth mentioning that for such transformations only one other organocatalytic system has been reported so far. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p>
収録刊行物
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- European Journal of Organic Chemistry
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European Journal of Organic Chemistry 2009 (22), 3683-3687, 2009-07-14
Wiley
