Regioselective synthesis of 2, 3, 4-or 2, 3, 5-trisubstituted pyrroles via [3, 3] or [1, 3] rearrangements of O-vinyl oximes

…, DS Mueller, RM Sachwani, R Kapadia…

Index: Wang, Heng-Yen; Mueller, Daniel S.; Sachwani, Rachna M.; Kapadia, Rachel; Londino, Hannah N.; Anderson, Laura L. Journal of Organic Chemistry, 2011 , vol. 76, # 9 p. 3203 - 3221

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Citation Number: 48

Abstract

The regioselective synthesis of 2, 3, 4-or 2, 3, 5-trisubstituted pyrroles has been achieved via [3, 3] and [1, 3] sigmatropic rearrangements of O-vinyl oximes, respectively. Iridium- catalyzed isomerization of easily prepared O-allyl oximes enables rapid access to O-vinyl oximes. The regioselectivity of pyrrole formation can be controlled by either the identity of the α-substituent or through the addition of an amine base. When enolization is favored, a [3, ...