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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