Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/8964
Title: Zinc-salen-catalyzed asymmetric alkynylation of alkyl acylsilanes
Authors: Li, FQ
Zhong, S
Lu, G
Chan, ASC
Keywords: Acylsilanes
Alkynylation
Asymmetric catalysis
Quaternary stereocenters
Salen ligands
Silylated propargylic alcohols
Issue Date: 2009
Publisher: Wiley-V C H Verlag Gmbh
Source: Advanced synthesis and catalysis, 2009, v. 351, no. 11-12, p. 1955-1960 How to cite?
Journal: Advanced Synthesis and Catalysis 
Abstract: Optically active tertiary propargylic alcohols are useful and versatile building blocks in organic synthesis, and their direct access by enantioselective addition of alkyne nucleophiles to ketones has achieved significant progress over the last ten years. In view of the potential applications of acylsilanes as useful synthetic equivalents of aldehydes, we described a general catalytic enantioselective addition of terminal alkynes to alkyl acylsilanes. After reaction optimization involving variation of solvent, tern-perature, catalyst ratio and various catalysts screen, the in situ generated Zn-salen complex was chosen as catalyst. With hexane as solvent, the silylated tertiary propargylic alcohols were obtained in satisfactory yields and ees for both aliphatic and aromatic alkynes.
URI: http://hdl.handle.net/10397/8964
DOI: 10.1002/adsc.200900177
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