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

被引：13

作者：

Lee, I-Chi ^{[1
]}

Zulueta, Medel Manuel L. ^{[1
,2
]}

Shie, Chi-Rung ^{[1
]}

Arco, Susan D. ^{[2
]}

Hung, Shang-Cheng ^{[1
,3
]}

机构：

[1] Acad Sinica, Genom Res Ctr, Taipei 115, Taiwan

[2] Univ Philippines, Inst Chem, Quezon City 1101, Philippines

[3] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 300, Taiwan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 22期

关键词：

ONE-POT PROTECTION; 4,6-O-BENZYLIDENE ACETALS; SUBSTITUTED 1,3-DIOXOLANES; ALUMINUM-CHLORIDE; CLEAVAGE; REGIOSELECTIVITY; BORANE; DERIVATIVES; HYDRIDE; ETHERS;

D O I：

10.1039/c1ob06056b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD3 revealed a retentive stereoselectivity probably through the rare S(N)i (internal nucleophilic substitution) mechanism. An S(N)1-like mechanism occurs in the acid-promoted regioselective BD3 center dot THF- or Et3SiD-reductive ring opening.

引用

收藏

页码：7655 / 7658

页数：4

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