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asymmetric autocatalysis. It is possible to discriminate the bulkiness of various substitu-
ents in the secondary alcohols by the comparison of the absolute confi gurations of sec -
alcohol used as chiral initiator and the obtained pyrimidyl alkanol. In addition, we
observed an unexpected reversal of the enantiofacial selectivity of chiral
β
- amino alcohol
catalysts by a smaller amount of achiral
β
-amino alcohol catalysts in the asymmetric
autocatalysis.
As described, asymmetric autocatalysis is closely related to the origin of the homochi-
rality of organic compounds.
ACKNOWLEDGMENT
Financial support by a Grant-in-Aid for Scientifi c Research from the Ministry of Educa-
tion, Culture, Sports, Science and Technology is gratefully acknowledged.
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