Highly Diastereoselective Reactions of Isoxazolidine-4,5-diols with Grignard Reagents: A New Approach to anti,syn-γ-Amino-α,β-diols,Synthesis

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Highly Diastereoselective Reactions of Isoxazolidine-4,5-diols with Grignard Reagents: A New Approach to anti,syn-γ-Amino-α,β-diols
Synthesis ( IF 2.6 ) Pub Date : 2020-10-29 , DOI: 10.1055/s-0040-1706543
Ondrej Záborský ₁ , Róbert Fischer ₁ , Lukáš Ďurina ₁ , Tomáš Malatinský ₁ , Ján Moncol ₂

Affiliation

Abstract

An investigation of the reaction of 3,4-trans-isoxazolidine-4,5-diols with Grignard reagents is described for the first time. Their resemblance to five-membered cyclic hemiacetals allows them to react as α-hydroxy-β-(hydroxyamino)aldehydes in a highly stereoselective manner, providing anti,syn-γ-(hydroxyamino)-α,β-diols in moderate yields and with good to excellent syn-diastereoselectivities, which can be improved by the addition of anhydrous cerium chloride. The obtained (hydroxyamino)diols serve as suitable precursors of anti,syn-γ-amino-α,β-diols that represent valuable scaffolds for the synthesis of various biologically active compounds.

Publication History

Received: 16 August 2020

Accepted after revision: 23 September 2020

Publication Date:
29 October 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

异恶唑烷-4,5-二醇与格氏试剂的高度非对映选择性反应：抗syn-γ-氨基-α，β-二醇的新方法

摘要

首次描述了3,4-反式-异恶唑烷-4,5-二醇与格利雅试剂的反应研究。它们与五元环半缩醛相似，可使其以高度立体选择性的方式作为α-羟基-β-（羟基氨基）醛反应，以适度的产率提供抗，顺-γ-（羟基氨基）-α，β-二醇。良好至优异的顺式非对映选择性，可通过添加无水氯化铈来改善。所获得的（羟基氨基）二醇用作抗，顺式-γ-氨基-α，β-二醇的合适前体，其代表用于合成各种生物活性化合物的有价值的支架。