C-alkylation of chiral tropane- and homotropane-derived enamines.

Journal article

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.

Authors: Hodgson, D; Charlton, A; Paton, R; Thompson, A

• Publication status: Published
• Journal: Journal of organic chemistry
• Volume: 78
• Issue: 4
• Pages: 1508-1518
• Publication date: 2013-02-01
• DOI: 10.1021/jo3025972
• EISSN: 1520-6904
• ISSN: 0022-3263
• Language: English
• Keywords: Ketones; Tropanes; Stereoisomerism; Amines; Aldehydes; Alkylation; Molecular Structure