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Stereoselective Synthesis of β-Hydroxyallenes with Multiple Contiguous Stereogenic Centers via Aldehyde Addition to α-Alkenyl-Substituted Zirconacyclopentenes

Yebing Zhou, Jingjin Chen, Chunbin Zhao, Erjuan Wang, Yuanhong Liu* and Yuxue Li

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China, Email:

Y. Zhou, J. Chen, C. Zhao, E. Wang, Y. Liu, Y. Li, J. Org. Chem., 2009, 74, 5326-5330.

DOI: 10.1021/jo900808k


Addition of α-alkenylzirconacyclopentenes to aldehyde enables a highly stereoselective synthesis of β-hydroxyallenes with multiple stereogenic centers including allenic axial chirality, as well as center chirality. Remarkably, the reaction occurs with completely different chemoselectivity in comparison with the usual alkyl- or aryl-substituted zirconacyclopentenes.

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Key Words

Allenes, Homoallylic Alcohols

ID: J42-Y2009-2230