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2005
Alcohols
Q 0230
35- 087
Synthesis of Chiral Hydroxythiolanes as Potential Catalysts for Asymmetric Organozinc Additions to Carbonyl Compounds. — Optically active hydroxythiolanes
are synthesized and checked as catalysts for asymmetric addition of diethylzinc (II) to
benzaldehyde (I). Unfortunately, all chiral compounds are inefficient. The yields are
generally low and the enantiomeric excess of alcohol (III) never exceeds 16% in spite
of applying a variety of solvents, additives, and conditions. Side-products are always
formed. In this type of reaction, neither is the hydroxy sulfide (sulfoxide) moiety capable of properly binding diethylzinc, nor does the sulfinyl group exert its normal stereoinduction. — (KIELBASINSKI*, P.; ALBRYCHT, M.; MIKOLAJCZYK, M.;
WIECZOREK, M. W.; MAJZNER, W. R.; FILIPCZAK, A.; CIOLKIEWICZ, P.;
Heteroat. Chem. 16 (2005) 2, 93-103; Cent. Mol. Macromol. Stud., Pol. Acad. Sci.,
PL-90-363 Lodz, Pol.; Eng.) — H. Hoennerscheid
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