Acid-Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water

被引:8
|
作者
Timmer, Brian J. J. [1 ]
Ramstrom, Olof [1 ,2 ,3 ]
机构
[1] KTH Royal Inst Technol, Dept Chem, Teknikringen 36, S-10044 Stockholm, Sweden
[2] Univ Massachusetts, Dept Chem, 1 Univ Ave, Lowell, MA 01854 USA
[3] Linnaeus Univ, Dept Chem & Biomed Sci, S-39182 Kalmar, Sweden
基金
瑞典研究理事会;
关键词
carbene ligands; carbohydrates; homogeneous catalysis; olefin metathesis; synthetic methods; CROSS-METATHESIS; ACTIVE CATALYSTS; RUTHENIUM; ALKYLIDENE; COMPLEXES; MOLYBDENUM; PERFORMANCE; AMPHIPHILE; DISCOVERY; EFFICIENT;
D O I
10.1002/chem.201903155
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The ability to use unprotected carbohydrates in olefin metathesis reactions in aqueous media is demonstrated. By using water-soluble, amine-functionalized Hoveyda-Grubbs catalysts under mildly acidic aqueous conditions, the self-metathesis of unprotected alkene-functionalized alpha-d-manno- and alpha-d-galactopyranosides could be achieved through minimization of nonproductive chelation and isomerization. Cross-metathesis with allyl alcohol could also be achieved with reasonable selectivity. The presence of small quantities (2.5 vol %) of acetic acid increased the formation of the self-metathesis product while significantly reducing the alkene isomerization process. The catalytic activity was furthermore retained in the presence of large amounts (0.01 mm) of protein, underlining the potential of this carbon-carbon bond-forming reaction under biological conditions. These results demonstrate the potential of directly using unprotected carbohydrate structures in olefin metathesis reactions under mild conditions compatible with biological systems, and thereby enabling their use in, for example, drug discovery and protein derivatization.
引用
收藏
页码:14408 / 14413
页数:6
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