1421636-84-1Relevant articles and documents
C-alkylation of chiral tropane- and homotropane-derived enamines
Hodgson, David M.,Charlton, Andrew,Paton, Robert S.,Thompson, Amber L.
, p. 1508 - 1518 (2013/05/09)
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.