Chiral Brønsted Acid Catalyzed Enantioselective Dehydrative Nazarov-type Electrocyclization of Aryl and 2-Thienyl Vinyl Alcohols,Journal of the American Chemical Society

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Chiral Brønsted Acid Catalyzed Enantioselective Dehydrative Nazarov-type Electrocyclization of Aryl and 2-Thienyl Vinyl Alcohols
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-04-09 , DOI: 10.1021/jacs.8b02339
Jianwen Jin ₁ , Yichao Zhao ₁ , Ali Gouranourimi ₂ , Alireza Ariafard ₂ , Philip Wai Hong Chan _{1,

3}

Affiliation

An efficient chiral Brønsted acid-catalyzed enantioselective dehydrative Nazarov-type electrocyclization (DNE) of electron-rich aryl- and 2-thienyl-β-amino-2-en-1-ols is described. The 4π conrotatory electrocyclization reaction affords access to a wide variety of the corresponding 1 H-indenes and 4 H-cyclopenta[ b]thiophenes in excellent yields of up to 99% and enantiomeric excess (ee) values of up to 99%. Experimental and computational studies based on a proposed intimate contact ion-pair species that is further assisted by hydrogen bonding between the amino group of the substrate cation and chiral catalyst anion provide insight into the observed product enantioselectivities.

中文翻译：

手性布朗斯台德酸催化芳基和 2-噻吩乙烯醇的对映选择性脱水纳扎罗夫型电环化

描述了一种有效的手性 Brønsted 酸催化的对映选择性脱水纳扎罗夫型电环化 (DNE) 的富电子芳基-和 2-噻吩基-β-氨基-2-en-1-ols。4π 旋转电环化反应可以以高达 99% 的优异收率和高达 99% 的对映体过量 (ee) 值获得各种相应的 1 H-茚和 4 H-环戊二烯 [b] 噻吩。基于提议的密切接触离子对物种的实验和计算研究，进一步由底物阳离子的氨基和手性催化剂阴离子之间的氢键辅助，提供了对观察到的产物对映选择性的深入了解。

更新日期：2018-04-09

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