Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions

被引：5
|
作者：
Dubey, Akhil K. [1 ]
Chowdhury, Raghunath [1 ,2 ]
机构：
[1] Bhabha Atom Res Ctr, Bioorgan Div, Mumbai 400085, Maharashtra, India
[2] Homi Bhabha Natl Inst, Mumbai 400094, Maharashtra, India
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 17卷
关键词：
beta-silyl alpha; beta-unsaturated carbonyl compounds; beta-silylnitroalkanes; chiral organosilanes; organocatalysis; solvent-free synthesis; ENANTIOSELECTIVE CONJUGATE ADDITIONS; ASYMMETRIC-SYNTHESIS; GRIGNARD-REAGENTS; PROTODESILYLATION; NITROMETHANE;
D O I：
10.3762/bjoc.17.177
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective 1,4-conjugate addition of nitromethane to beta-silyl alpha,beta-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of beta-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5%) under solvent-free conditions at room temperature. Control experiments reveal that the presence of a beta-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions.
引用
收藏
页码：2642 / 2649
页数：8
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