<i>C</i>‑Alkylation
of Chiral Tropane-
and Homotropane-Derived Enamines
- Publication date
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Abstract
The synthesis and alkylation of chiral, nonracemic tropane-
and
homotropane-derived enamines is examined as an approach to enantioenriched
α-alkylated aldehydes. The two bicyclic N auxiliaries, which
differ by a single methylene group, give opposite senses of asymmetric
induction on alkylation with EtI and provide modestly enantioenriched
2-ethylhexanal (following hydrolysis of the alkylated iminium). The
observed stereoselectivity is supported by density functional studies
of ethylation for both enamines