115377-36-1Relevant articles and documents
Effect of Crown Ethers on the Regioselectivity of Allylation of Benzaldehyde with Allylic Barium Reagents
Yanagisawa, Akira,Yamada, Yasuhiro,Yamamoto, Hisashi
, p. 1090 - 1092 (1997)
An increase of α-regioselectivity was observed in the reaction of allylic barium reagents with aldehydes employing crown ether as an additive. For example, an α/γ regioselectivity was improved to 98/2 from 92/8, when an equimolar amount of 18-crown-6 was added to geranylbarium reagent in THF at -78°C prior to the reaction with benzaldehyde.
Forging C-C Bonds with Hindered Nucleophiles and Carbonyl Electrophiles: Reactivity and Selectivity of Allylic Tin Reagents/n-BuLi
Cormier, Morgan,Ahmad, Maha,Maddaluno, Jacques,De Paolis, Micha?l
, p. 4920 - 4927 (2018/02/07)
Under activation with n-BuLi, trialkylstannanes containing crotyl-, geranyl-, and phenyldienylmethyl appendages were reacted with efficiency and selectivity to various ketone and enone electrophiles with low reactivity. The straightforward process gives access to tertiary alcohols that are vicinal to quaternary carbons. With α,α′-dimethoxy-γ-pyrone, on the other hand, the grafting of a dienyl side chain was effected to prepare dienyl α′-methoxy-γ-pyrone in a stereo- and regioselective and convergent manner. Furthermore, the advantages of this route were highlighted for the preparation of organolithium species at low temperature with the formation of a minimum amount of salts. Synthetic manipulations were demonstrated to illustrate the potential of the chemistry for constructing acyclic and cyclic terpene scaffolds.
Allylbarium in Organic Synthesis: Unprecedented α-Selective and Stereospecific Allylation of Carbonyl Compounds
Yanagisawa, Akira,Habaue, Shigeki,Yamamoto, Hisashi
, p. 8955 - 8956 (2007/10/02)
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