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Synlett 1998; 1998(9): 958-960
DOI: 10.1055/s-1998-5737
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Diastereoselective Aldol Reaction of Tin Enolate of Cyclohexanone Catalyzed by Metal Triflates

Akira Yanagisawa* , Kazutaka Kimura, Yoshinari Nakatsuka, Hisashi Yamamoto
  • *Graduate School of Engineering, Nagoya University, CREST, Japan Science and Technology Corporation (JST), Chikusa, Nagoya 464-8603, Japan
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Publication Date:
31 December 2000 (online)

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The diastereoselective aldol reaction of tributyltin enolate of cyclohexanone with benzaldehyde was studied in the presence of a catalytic amount of various metal triflates. The highest anti selectivity was observed with Pd(OTf)2, while Zn(OTf)2 in THF showed moderate syn selectivity. The use of (S,S)- i Pr-pybox 3 ⋅ Cu(OTf)2 complex as a catalyst preferentially produced the optically active syn aldol adduct with 84% ee.

diastereoselective aldol reaction - tin enolates - metal triflates - aldehydes - chiral bis(oxazoline)