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^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal Article › peer-review

19 Scopus citations

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.

Original language	English
Pages (from-to)	7655-7658
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	22
DOIs	https://doi.org/10.1039/c1ob06056b
State	Published - 26 10 2011
Externally published	Yes

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title = "Deuterium-isotope study on the reductive ring opening of benzylidene acetals",

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 - Lee, I. Chi

AU - Zulueta, Medel Manuel L.

AU - Shie, Chi Rung

AU - Arco, Susan D.

AU - Hung, Shang Cheng

PY - 2011/10/26

Y1 - 2011/10/26

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/80054996701

U2 - 10.1039/c1ob06056b

DO - 10.1039/c1ob06056b

M3 - 文章

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AN - SCOPUS:80054996701

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EP - 7658

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ER -

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

Abstract

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