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2004
C-C bond formation
O 0282
Yb(OTf)3—TMSCl, a Novel Catalytic System in Cross-Aldol Reactions. — The
reaction of cyclohexanones such as (I) or (VI) with aldehydes in the pres44- 062 cross-aldol
ence of 0.1 equivalents of Yb(OTf)3 and 3 equivalents of TmsCl gave the corresponding
aldol adducts (IV), (V) or (VIII). The function of TmsCl is unclear; however 3 equiv.
are needed for the activation of both carbonyl groups as well as improvement of the
yield. In the absence of Tms-Cl only 0-6% of the product are obtained. When the reaction is performed with cycloheptanone and cyclooctanone (VI), additionally the products (IX) are isolated arising from incorporation of an Et2N-CH=CH2 intermediate
formed by attack of TmsCl to NEt3. — (KAGAWA, N.; TOYOTA, M.; IHARA*, M.;
Aust. J. Chem. 57 (2004) 7, 655-657; Dep. Org. Chem., Grad. Sch. Pharm. Sci.,
Tohoku Univ., Aoba, Sendai 980, Japan; Eng.) — Kieslich
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