Lewis acid-catalyzed enantiospecific [3 + 2] annulations of γ-butyrolactone fused cyclopropanes with aromatic aldehydes: synthesis of chiral furanolignans†,Organic & Biomolecular Chemistry

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Lewis acid-catalyzed enantiospecific [3 + 2] annulations of γ-butyrolactone fused cyclopropanes with aromatic aldehydes: synthesis of chiral furanolignans†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-03-22 00:00:00 , DOI: 10.1039/c8ob00455b
Yue Shen _{1,

2,

3,

4,

5} , Peng-Fei Yang _{1,

2,

3,

4,

5} , Gaosheng Yang _{1,

2,

3,

4,

5} , Wen-Long Chen _{1,

2,

3,

4,

5} , Zhuo Chai _{1,

2,

3,

4,

5}

Affiliation

An enantiospecific [3 + 2] annulation of γ-butyrolactone fused cyclopropanes with aromatic aldehydes was realized under Lewis acid catalysis. This method provides facile access to a series of chiral furanolignan derivatives bearing multiple contiguous stereogenic centers in good-to-excellent yields, exclusive diastereoselectivities and excellent enantiopurities under mild reaction conditions. Elaboration work on the product of this reaction delivers stereoisomeric analogues of (+)-virgatusin and suggests a structural revision might be necessary for a previously reported isolated natural product.

中文翻译：

路易斯酸催化的γ-丁内酯稠合环丙烷与芳族醛的对映体特异性[3 + 2]取代：手性呋喃喃聚糖的合成†

在路易斯酸催化下，实现了γ-丁内酯稠合环丙烷与芳族醛的对映体特异性[3 + 2]环化反应。该方法可在温和的反应条件下轻松获得一系列具有多个连续的立体异构中心的手性呋喃并呋喃聚糖衍生物，并具有良好至优异的产率，独特的非对映选择性和出色的对映体纯度。对该反应产物的精制工作可提供（+）-virgatusin的立体异构体类似物，并建议对先前报道的分离的天然产物进行结构修改可能是必要的。

更新日期：2018-03-22

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