Stereoselective dioxirane hydroxylations and the synthesis of tripod boronic acid esters

被引:4
|
作者
D'Accolti, Lucia
Fiorentino, Michele
Fusco, Caterina
Capitelli, Francesco
Curci, Ruggero
机构
[1] Univ Bari, Dipartmento Chim, I-70126 Bari, Italy
[2] CNR, ICCOM, Bari Sect, I-70126 Bari, Italy
[3] CNR, Ist Cristallog, I-70123 Bari, Italy
关键词
boronic acids; borates; BLA; dioxiranes; methyl(trifluoromethyl)dioxirane; stereoselective oxidations;
D O I
10.1016/j.tetlet.2007.03.101
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyl(trifluoromethyl)dioxirane (TFDO, 1b), a powerful yet selective oxidant, was employed to achieve in high yield the direct stereoselective hydroxylation at tert-CH of cis,cis-1,3,5-trimethylcyclohexane (4), yielding triol 7 bearing all-axial disposition of the three OH groups. Similarly, TFDO oxidation of 1,3- and of 1,4-dimethylcyclohexane gave the corresponding Z-diols 5 and 6, respectively. Triol 7 was a convenient starting material to synthesize a novel borate-that is, 1-bora-2,8,9-trioxa-3,5,7-trimethyl-adamantane (8)-having a peculiar cage-shaped 'tripod' structure. From triol 7, novel tripod arylboronic Bronsted-assisted Lewis acids (BLA) could be obtained, as exemplified by 10a and 10b. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3575 / 3578
页数:4
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