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
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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