Organocatalytic Asymmetric Tandem Nazarov Cyclization/Semipinacol Rearrangement: Rapid Construction of Chiral Spiro[4.4]nonane-1,6-diones
Journal of the American Chemical Society2015Vol. 137(26), pp. 8344–8347
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Bin‐Miao Yang, Peijun Cai, Yong‐Qiang Tu, Zhi‐Xiang Yu, Zhi‐Min Chen, Shuanghu Wang, Shao‐Hua Wang, Fu‐Min Zhang
Abstract
A novel organocatalytic asymmetric tandem Nazarov cyclization/semipinacol rearrangement reaction using "unactivated" substrates has been developed, generating a series of chiral spiro[4.4]nonane-1,6-diones in up to 96% yield and 97% enantiomeric excess. Significantly, it is the first direct example for asymmetric synthesis of cyclopentanones with four stereocenters using Nazarov cyclization. DFT calculations have been applied to understand the reaction mechanism, stereochemistry, and substituent effects.
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