C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines

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• 作者：David M. Hodgson ; Andrew Charlton ; Robert S. Paton ; Amber L. Thompson
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：February 15, 2013
• 年：2013
• 卷：78
• 期：4
• 页码：1508-1518
• 全文大小：546K
• 年卷期：v.78,no.4(February 15, 2013)
• ISSN：1520-6904

文摘

The synthesis and alkylation of chiral, nonracemic tropane- and homotropane-derived enamines is examined as an approach to enantioenriched 伪-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.