Me(CHCl)SiCF Facilitated Tandem Synthesis of Oxasilacycles Featuring a Trifluoromethyl Group.
作者信息
Lei Chuan-Wen, Wang Xi-Yu, Mu Bo-Shuai, Yu Jin-Sheng, Zhou Ying, Zhou Jian
机构信息
College of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, China.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development; Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University, Shanghai 200062, China.
出版信息
Org Lett. 2022 Nov 18;24(45):8364-8369. doi: 10.1021/acs.orglett.2c03393. Epub 2022 Nov 1.
An unprecedented tandem trifluoromethylsilylation/intramolecular S2 substitution sequence was realized by using bifunctional reagent Me(CHCl)SiCF, allowing efficient construction of valuable trifluoromethylated oxasilacyclohexanes that are difficult to access by known methods. Initial attempts into developing asymmetric variant reveal that using cinchonine-derived dimeric PTC catalyst could afford chiral oxasilacyclohexanes in up to 92% enantiomeric excess.
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