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Synlett 1998; 1998(8): 924-926
DOI: 10.1055/s-1998-1815
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Functionalized Triarylcarbenium Ions as Catalysts in Mukaiyama Aldol Addition: Effects of Counter Ions and Silyl Groups on the Intervention of Silyl Catalysis

Chien-Tien Chen* , Shi-Deh Chao, Kuao-Chung Yen
  • *Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan 117; Fax 011-886-2-29 32 42 49; E-mail: chefv043@scc.ntnu.edu.tw
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Publication Date:
31 December 2000 (online)

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Stereochemical studies have indicated that functionalized Tr+SbCl6 - may serve as efficient aldol reaction catalysts by judicious choice of a silyl component. The aldol addition between TMS ketene acetal derived from γ-butyrolactone and benzaldehyde provided the silyl aldolates with high syn diastereoselectivities.

Meerwein salts - ionization - trityl ions - diastereoselective - β-hydroxylactones