- C-alkylation of chiral tropane- and homotropane-derived enamines.
C-alkylation of chiral tropane- and homotropane-derived enamines.
The Journal of organic chemistry (2013-01-30)
David M Hodgson, Andrew Charlton, Robert S Paton, Amber L Thompson
PMID23356473
초록
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.
MATERIALS