Premium
Zinc‐Salen‐Catalyzed Asymmetric Alkynylation of Alkyl Acylsilanes
Author(s) -
Li FengQuan,
Zhong Shi,
Lu Gui,
Chan Albert S. C.
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900177
Subject(s) - chemistry , enantioselective synthesis , catalysis , alkyne , alkynylation , alkyl , organic chemistry , nucleophile , solvent , zinc , combinatorial chemistry
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, temperature, 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 ee s for both aliphatic and aromatic alkynes.