Organic Letters
Organic Letters
5 years ago

Atropisomeric Chiral Diiododienes (Z,Z)-2,3-Di(1-iodoalkylidene)tetralins: Synthesis, Enantiomeric Resolution, and Application in Asymmetric Catalysis

Atropisomeric Chiral Diiododienes (Z,Z)-2,3-Di(1-iodoalkylidene)tetralins: Synthesis, Enantiomeric Resolution, and Application in Asymmetric Catalysis
Masamichi Ogasawara, Naoko Takenaga, Hao Hu, Kiyohiko Nakajima, Hikaru Nakajima, Toshifumi Dohi, Yasuyuki Kita, Yuta Amano, Hirotaka Sasa, Tamotsu Takahashi
The C2-symmetric tetralin-fused 1,4-diiodo-1,3-butadiene derivatives, (Z,Z)-2,3-di(1-iodoalkylidene)tetralin 1a–c, are atropisomeric and can be resolved into the two persistent axially chiral enantiomers by HPLC on a chiral stationary phase. The enantiomerically pure compounds can serve as chiral organocatalysts for dearomatizing spirolactonization to show good performance in up to 73% ee.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01876

DOI: 10.1021/acs.orglett.7b01876

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