Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: total synthesis of acremoauxin A and oxazinin 3

JM Richter, BW Whitefield, TJ Maimone…

Index: Richter, Jeremy M.; Whitefield, Brandon W.; Maimone, Thomas J.; Lin, David W.; Castroviejo, M. Pilar; Baran, Phil S. Journal of the American Chemical Society, 2007 , vol. 129, # 42 p. 12857 - 12869

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Citation Number: 128

Abstract

Full details are provided for a recently invented method to couple indoles and pyrroles to carbonyl compounds. The reaction is ideally suited for structurally complex substrates and exhibits high levels of chemoselectivity (functional group tolerability), regioselectivity (coupling occurs exclusively at C-3 of indole or C-2 of pyrrole), stereoselectivity (substrate control), and practicality (amenable to scaleup). In addition, quaternary stereocenters are ...