ChemInform Abstract: Syn-Selective Nitro-Michael Addition of Furanones to β,β-Disubstituted Nitroalkenes Catalyzed by epi-Quinine Derivatives

Autor: Hayato Kitaura, Yasuo Hatanaka, Tohru Sekikawa, Takayuki Kitaguchi, Tatsuya Minami
Rok vydání: 2016
Předmět:
Zdroj: ChemInform. 47
ISSN: 0931-7597
DOI: 10.1002/chin.201643101
Popis: Epi-quinine-catalyzed asymmetric nitro-Michael addition of furanones to β,β,-disubstituted nitroalkenes is described. The reaction proceeded smoothly with 1–5 mol % loadings of epi-quinine catalysts at room temperature, giving the corresponding Michael adducts in high yields (72–93%) with extremely high diastereo- and enantioselectivities (>98/2 dr, syn major; 95–99% ee). This reaction provides an effective and straightforward method for constructing all-carbon quaternary stereogenic centers adjacent to oxygen-containing quaternary stereogenic centers.
Databáze: OpenAIRE