tert‐Butyldimethylsilyl‐Directed Highly Enantioselective Approach to Axially Chiral α‐Allenols |
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| Authors: | Juntao Ye Wu Fan Prof Dr Shengming Ma |
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| Institution: | 1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu, Shanghai 200032 (P.R. China), Fax: (+86)?21‐6416‐7510;2. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062 (P.R. China) |
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| Abstract: | A highly efficient and enantioselective synthesis of axially chiral α‐allenols was realized in practical yields with 96–99 % ee or de from TBS‐protected propargylic alcohols, aldehydes, and a commercially available, inexpensive, chiral, secondary amine (S)‐α,α‐diphenylprolinol or its enantiomer followed by desilylation. The easily removable TBS group not only acts as a protecting group, but also as a possible sterically directing group for the excellent enantioselectivity and in situ prevention of possible allene racemization. |
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| Keywords: | allenes amines chirality enantioselectivity steric hindrance |
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