期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 39, 页码 10167-10172出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901310
关键词
aldehydes; asymmetric catalysis; flow reactors; Mannich reactions; organocatalysis
资金
- Ministerio de Ciencia a Innovacion [CTQ2008-00947/13QU]
- Department d'Innovacio. Universitats Empresa [2005SGR225]
- Consolider Ingenio 2010 [CSD2006-0003]
- Institute of Chemical Research of Catalonia (ICIQ) Foundation
- ICIQ foundation
The fast and highly stereoselective Mannich reaction of aldehydes and ketones with the N-(p-methoxyphenyl) ethyl glyoxylate imine catalyzed by polystyrene. resins functionalized with (2SAR)-hydroxyproline is reported The effect of the nature of the linker connecting proline with the polymeric backbone has been studied, and a 1,2,3-triazole linker constructed front azidomethyl polystyrene and O-propargyl hydroxyproline turns out to be optimal for catalytic activity and enantioselectivity. With aldehyde donors. fast reactions leading to complete con-version in 1-3 h are recorded in DMF Willi ketone donors. the reactions tend to be slower, but can be efficiently accelerated (six-membered ring cycloalkanones) by low-power microwave irradiation. This approach, which greatly facilitates product isolation since the catalyst is removed by simple filtration. has allowed the implementation of the reactions of aldehyde Substrates in a continuous-flow. single-pass system In this manner, the Continuous synthesis of the enantiomerically and diastereomerically pure adducts (synlann > 97:3: ee>99%) has been achieved at room temperature with residence times of 6.0 mm. This methodology has allowed for the preparation of up to 7.8 mmol elf the desired Mannich adduct through the use of 046 mmol of catalytic resin (5 9 mol%), in at greatly simplified experimental protocol that avoids purification steps
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