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Direct Regio‐, Diastereo‐, and Enantioselective Vinylogous Michael Addition of Prochiral 3‐Alkylideneoxindoles to Nitroolefins
Author(s) -
Rassu Gloria,
Zambrano Vincenzo,
Pinna Luigi,
Curti Claudio,
Battistini Lucia,
Sartori Andrea,
Pelosi Giorgio,
Zanardi Franca,
Casiraghi Giovanni
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300168
Subject(s) - stereocenter , chemistry , enantioselective synthesis , michael reaction , stereoselectivity , context (archaeology) , synthon , isomerization , olefin fiber , stereochemistry , organocatalysis , organic chemistry , catalysis , paleontology , biology
3‐Alkylidene‐2‐oxindoles represent a simple, yet enabling subfamily of indole alkaloids, and their ability to react as electron‐poor acceptors has largely been investigated. In contrast, their utility as pronucleophilic synthons remains elusive. In this context, the present article describes the successful execution of the direct, organocatalytic asymmetric Michael addition of prochiral 3‐alkylideneoxindoles to nitroolefins. A variety of γ‐substituted alkylideneoxindoles carrying two stereocenters at both the γ‐ and δ‐carbon sites was assembled with excellent stereoselectivity and without olefin isomerization or stereochemical ablation.