RESUMO
A DMP-initiated metal-free effective ß,γ-asymmetric spirocyclopropanation of propanols strategy using oxidative iminium activation is described. This process has been realized by a synergistic amine-catalyzed one-pot cascade oxidation-Michael addition cyclopropanation for "one-pot" access to various spirocyclopropyl propionaldehydes/propanols from diverse 3-arylpropanols and α-brominated active methylene compounds under mild conditions and with high enantioselectivity (ee up to >99%).
RESUMO
Saturated bicyclic amines are increasingly targeted to the pharmaceutical industry as sp3-rich bioisosteres of anilines. Numerous strategies have been established for the preparation of bridgehead aminobicyclics. However, methods to assemble the bridge-amino hydrocarbon skeleton, which serves as a meta-substituted arene bioisostere, are limited. Herein, a general approach to access 2-aminobicyclo[2.1.1]hexanes (aminoBCHs) by titanium-catalyzed formal [2π + 2σ] cycloaddition of bicyclo[1.1.0]butanes and 2-azadienes was developed. Simple derivatization of aminoBCHs leads to various medicinally and agrochemically important analogues.
RESUMO
A one-pot three-component reaction based on an oxidative dearomatization strategy has been performed to provide facile access to 5-hydroxyindole derivatives through a ZnI2-catalyzed tandem process. The multi-unit reactions for the construction of a new C-C bond and two C-N bonds are simple and efficient under mild conditions, and the yield of the target product is as high as 91%.