A phosphine-catalyzed tandem cyclization reaction has been developed to provide a series of chromeno [4,3-b]pyrrole derivatives, which contain three consecutive asymmetric centers. The reaction has a good yield, excellent stereoselectivity, and Z/E selectivity. The new method is simple, requires only mild conditions, and shows tolerance for various functional groups. Similarly, this reaction can be catalyzed by a chiral phosphine catalyst to achieve asymmetric synthesis. cascade cycloaddition strategy for facily synthesizing chromenopyrrole derivatives from aldimine esters and δ-acetoxy allenoates. In particular, a wide range of products have been afforded in generally good yields with excellent diastereoselectivities. In addition, by using a chiral phosphine catalyst, the cycloaddition reaction can also initially realize the asymmetric synthesis of chromeno [4,3-b]pyrrole. This protocol can be expected to find wide synthetic application because of its simple operation, mild reaction conditions, high efficiency, and high chemo-and enantioselectivity.
A catalyst-free [3
+ 2] cycloaddition reaction of electron-deficient
alkynes and
o
-hydroxyaryl azomethine ylides in water
was developed, affording pyrroline derivatives in moderate to high
yields (up to 90%).
Text. A general method for the synthesis of structural diversity and complexity of azepines from aldimine esters and β'-acetoxy allenoates is reported. Under phosphine catalysis, a [4 + 3] cycloaddition for the formation of 1,3-dihydro-2H-azepine-2,2,4-tricarboxylates was achieved with broad substrate scope under mild reactions. A switchable process was given and a variety of important 2,3-dihydrochromeno[4,3-b] azepin-6(1H)-ones were selectively formed when the reaction was performed in the presence of Cs 2 CO 3 and PPh 3 , which involved an intramolecular ester group migration and subsequent lactonization of 1,3-dihydro-2Hazepine-2,2,4-tricarboxylates. Besides easy handle process, high synthetic value of resulting products, it is worth to note that this work showed the novel example of 1,5-ethoxycarbonyl migration.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.