Abstract
In this account, recent accomplishments in the field of target-oriented
synthesis involving allenes are summarized. Allenic α-amino
acid derivatives 9, which are of interest
as possible vitamin B6 decarboxylase inhibitors, were
prepared by 1,6-addition of the cyano-Gilman reagent t-Bu2CuLi·LiCN to
2-amino-substituted enynoates 8, and selective
deprotection at either the amino or the ester group was realized.
2,5-Dihydrofurans 18 were obtained by cyclization
of the corresponding α-hydroxyallenes; for this step, new methods
(treatment with hydrogen chloride gas or acidic ion exchange resin;
gold(III)-chloride catalysis) were developed. The 2-hydroxy-3,4-dienoates 14 were obtained by diastereoselective
oxidation of titanium enolates formed from 3,4-dienoates 12 with dimethyl dioxirane (DMDO),
whereas hydroxyallenes 16 were prepared
by copper-mediated SN2′-substitution of propargylic
epoxides 15.
Key words
allenes - amino acids - gold catalysis - 2,5-dihydrofurans - organocopper reagents
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