Stripping off water at ambient temperature: Direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate

被引：56

作者：

Chen, CT ^{[1
]}

Weng, SS

Kao, JQ

Lin, CC

Jan, MD

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei, Taiwan

[2] Acad Sinica, Inst Chem, Taipei, Taiwan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 15期

关键词：

D O I：

10.1021/ol051178z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aromatic aldehydes can be readily protected as acetals with 1,2- and 1,3-diols by using vanadyl triflate as a catalyst in CH3CN at ambient temperature. Carbohydrate-based 1,2- and 1,3-diols can similarly be protected in good to excellent yields. The catalyst can be readily recovered from the aqueous layer. In combination with vanadyl triflate-catalyzed sequential regioselective, reductive acetal opening and chemoselective acylations, the title method allows for differential functionalization of all four hydroxyl units in a given glucopyranoside.

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页码：3343 / 3346

页数：4

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