Deuterium-isotope study on the reductive ring opening of benzylidene acetals

I. Chi Lee; Medel Manuel L. Zulueta; Chi Rung Shie; Susan D. Arco; Shang Cheng Hung

doi:10.1039/c1ob06056b

Deuterium-isotope study on the reductive ring opening of benzylidene acetals

I. Chi Lee, Medel Manuel L. Zulueta, Chi Rung Shie, Susan D. Arco, Shang Cheng Hung^*

^*此作品的通信作者

研究成果: 期刊稿件 › 文章 › 同行評審

18 引文斯高帕斯（Scopus）

摘要

Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD ₃ revealed a retentive stereoselectivity probably through the rare S _Ni (internal nucleophilic substitution) mechanism. An S _N1-like mechanism occurs in the acid-promoted regioselective BD ₃·THF- or Et ₃SiD-reductive ring opening.

原文	英語
頁（從 - 到）	7655-7658
頁數	4
期刊	Organic and Biomolecular Chemistry
卷	9
發行號	22
DOIs	https://doi.org/10.1039/c1ob06056b
出版狀態	已出版 - 26 10 2011
對外發佈	是

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abstract = "Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD 3 revealed a retentive stereoselectivity probably through the rare S Ni (internal nucleophilic substitution) mechanism. An S N1-like mechanism occurs in the acid-promoted regioselective BD 3·THF- or Et 3SiD-reductive ring opening.",

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AU - Zulueta, Medel Manuel L.

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AU - Arco, Susan D.

AU - Hung, Shang Cheng

PY - 2011/10/26

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AB - Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD 3 revealed a retentive stereoselectivity probably through the rare S Ni (internal nucleophilic substitution) mechanism. An S N1-like mechanism occurs in the acid-promoted regioselective BD 3·THF- or Et 3SiD-reductive ring opening.

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Deuterium-isotope study on the reductive ring opening of benzylidene acetals

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