期刊
SYNTHESIS-STUTTGART
卷 46, 期 24, 页码 3399-3407出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1378618
关键词
asymmetric catalysis; alcohols; organocatalysis; carbocations; alkylation
资金
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CTQ2010-20387]
- Spanish Ministerio de Ciencia e Innovacion (MICINN) (project Consolider Ingenio) [CSD2007-00006]
- FEDER
- Generalitat Valenciana [PROMETEO 2009/039]
- University of Alicante [GRE12-03]
The first organocatalyzed asymmetric alkylation of activated methylene compounds using benzylic and allylic alcohols as alkylating agents through dual hydrogen bond activation in an S(N)1-type reaction is reported. This green protocol employs a bis(2-aminobenzoimidazole) in combination with an achiral BrOnsted acid as a bifunctional catalytic system and gives the alkylation products with moderate to good enantioselectivities. Although the scope of the reaction is limited, this methodology can be considered as complementary to existing metal-catalyzed processes. In addition, modest results were obtained in a first attempt to perform a metal-free asymmetric Tsuji-Trost reaction using allylic alcohols. Finally, the recovery and reusability of the organocatalyst is also achieved.
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