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Stereoselective Iodolactonization of 4‐Allenoic Acids with Efficient Chirality Transfer: Development of a New Electrophilic Iodination Reagent |
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| Authors: | Xiaobing Zhang Prof Dr Chunling Fu Prof Yihua Yu Prof Dr Shengming Ma |
| Institution: | 1. Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P.R. China), Fax: (+86)?21‐6260‐9305;2. Shanghai Key Laboratory of Functional, Magnetic Resonance Imaging, Department of Physics, East China Normal University, Shanghai 200062 (P.R. China) |
| Abstract: | A highly stereoselective iodolactonization of 4‐allenoic acids with a new sterically demanding electrophilic iodination reagent to afford optically active γ‐butyrolactones has been developed. The reaction shows high efficiency of axial chirality transfer and excellent Z/E selectivity and has been applied to the synthesis of chiral cis‐β,γ‐disubstituted γ‐butyrolactones to give very high diastereomeric and enantiomeric excess values. The reaction has been successfully utilized in the synthesis of naturally occurring compounds (+)‐cis‐whisky lactone and (+)‐cis‐3‐methyl‐4‐decanolide. |
| Keywords: | allenes chirality cyclization electrophilic addition iodine |