A 4‐Hydroxypyrrolidine‐Catalyzed Mannich Reaction of Aldehydes: Control of <i>anti‐</i>Selectivity by Hydrogen Bonding Assisted by Brønsted Acids
書誌事項
- 公開日
- 2010-05-04
- 権利情報
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- http://onlinelibrary.wiley.com/termsAndConditions#vor
- DOI
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- 10.1002/chem.200903537
- 公開者
- Wiley
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説明
<jats:title>Abstract</jats:title><jats:p>An <jats:italic>anti</jats:italic>‐selective Mannich reaction of aldehydes with <jats:italic>N</jats:italic>‐sulfonyl imines has been developed by using a 4‐hydroxypyrrolidine in combination with an external Brønsted acid. The catalyst design is based on three elements: the α‐substituent of the pyrrolidine, the 4‐hydroxy group, and the Brønsted acid, the combination of which is essential for high chemical and stereochemical efficiency. The reaction works with aromatic aldehyde‐derived imines, which have rarely been employed in previously reported enamine‐based <jats:italic>anti</jats:italic>‐Mannich reactions. Additionally, both <jats:italic>N</jats:italic>‐tosyl and <jats:italic>N</jats:italic>‐nosyl imines can be successfully used and the Mannich adducts can be easily reduced or oxidized, and after <jats:italic>N</jats:italic>‐deprotection the corresponding β‐amino acids and β‐amino alcohols can be obtained with good yields. The results also show that this ternary catalytic system may be practical in other enamine‐based reactions.</jats:p>
収録刊行物
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- Chemistry – A European Journal
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Chemistry – A European Journal 16 (18), 5333-5342, 2010-05-04
Wiley
