Chiral silicon groups possessing an asymmetric and chelating alkoxymethyl substituent at silicon have been prepared, and it was shown that these groups may have substantial utility as stereodirecting auxiliaries. For the 1,2-addition of organometallic species to chiral acylsilanes, auxiliaries with a single stereogenic center at position 6 with respect to the reactive carbonyl C atom proved particularly valuable. Compounds with such auxiliaries are easily accessible in enantiomerically pure form, and the chiral groups induce π-facial selectivities of as high as 98:2. In an example it is shown that chiral 1,6-induction may dominate over 1,5-induction.

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