Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles

Abstract

The aldehyde 2-formyl-2-(pent-4-enyl)-1,3-dithiane 1, containing both alkene and aldehyde functional groups, is a good substrate for intramolecular dipolar cycloaddition reactions after condensation with various N-alkyl α-amino-esters. This paper reports the optimization, scope and stereoselectivity of this reaction to give octahydroindoles (2-azabicyclo[4.3.0]nonanes).

Total Synthesis of (−)‐Lycoposerramine‐S

“…11 As shown in Scheme , the reaction of 11 with 12 unexpectedly afforded a 2,5‐ cis ‐disubstituted pyrrolidine via the Z ‐ylide intermediate 12. 13…”

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

“…Coldham, et al [101] have studied the intramolecular azomethine ylide cycloaddition reaction. A convenient and direct approach to the required dipole uses the condensation of a -aminoester with an aldehyde.…”

Regio‐ and stereoselective synthesis of 1‐benzopyrano[2,3‐b]pyrrolo[2,3‐d]pyridines: A microwave‐accelerated intramolecular [3+2] cycloaddition reaction of azomethine ylide

“…Intramolecular nitrone–olefin cycloaddition reaction has been widely used for the synthesis of complex heterocyclic compounds including alkaloids [2, 3], modified nucleosides [4], β‐lactam antibiotics [5], and natural products [6]. O ‐Allylated salicylaldehyde [7, 8], 4‐allylamino‐3‐formyl‐α‐pyrone [9], and 2‐allylamino‐3‐formylchromone [10] have been used in intramolecular [3+2] nitrone–olefin cycloaddition reaction for the synthesis of isoxazolidines fused with different heterocycles [11–15]. Analogous pyrrolidine derivatives, which may be obtained by azomethine ylide–olefin cycloaddition, possess antiviral [16] and local anesthetic activities [17].…”