Forging C–C Bonds with Hindered Nucleophiles and Carbonyl Electrophiles: Reactivity and Selectivity of Allylic Tin Reagents/ n -BuLi - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organometallics Année : 2017

Forging C–C Bonds with Hindered Nucleophiles and Carbonyl Electrophiles: Reactivity and Selectivity of Allylic Tin Reagents/ n -BuLi

Résumé

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.

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Chimie organique
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Dates et versions

hal-02019144 , version 1 (14-02-2019)

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Citer

Morgan Cormier, Maha Ahmad, Jacques Maddaluno, Michaël de Paolis. Forging C–C Bonds with Hindered Nucleophiles and Carbonyl Electrophiles: Reactivity and Selectivity of Allylic Tin Reagents/ n -BuLi. Organometallics, 2017, 36 (24), pp.4920-4927. ⟨10.1021/acs.organomet.7b00765⟩. ⟨hal-02019144⟩
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