A Photochemical Route to 3- and 4-Hydroxy Derivatives of 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry,The Journal of Organic Chemistry

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A Photochemical Route to 3- and 4-Hydroxy Derivatives of 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-12-19 00:00:00 , DOI: 10.1021/acs.joc.7b02559
Zong Chang ₁ , France Boyaud ₁ , Régis Guillot ₂ , Thomas Boddaert ₁ , David J. Aitken ₁

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Short gram-scale syntheses of both enantiomers of 2-amino-3-hydroxycyclobutane-1-carboxylic acid and of 2-amino-4-hydroxycyclobutanecarboxylic acid with an all-cis geometry are described. The sequences feature highly endo-selective [2 + 2]-photocycloaddition reactions followed by fully regioselective ring opening/Hofmann rearrangement/nitrogen protection, in a consecutive or one-pot protocol, followed by efficient resolution using a chiral oxazolidinone.

中文翻译：

具有全顺式几何构型的2-氨基环丁烷-1-羧酸3-和4-羟基衍生物的光化学路线

描述了具有全顺式几何构型的2-氨基-3-羟基环丁烷-1-羧酸和2-氨基-4-羟基环丁烷羧酸的对映体的短克级合成。该序列具有高度内选择性[2 + 2]-光环加成反应，然后在连续或一锅操作方案中进行完全区域选择性的开环/霍夫曼重排/氮保护，然后使用手性恶唑烷酮进行高效拆分。

更新日期：2017-12-19

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