期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 10, 期 38, 页码 7721-7729出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob26185e
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资金
- Deutsche Forschungsgemeinschaft [Ki 397/16-1]
- Fonds der Chemischen Industrie
The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The size of the substituent in the beta-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products.
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