Enantioselective nitroso-Diels-Alder reaction and its application for the synthesis of (-)-peracetylated conduramine A-1.
Cu(I)-catalyzed enantioselective nitroso-Diels-Alder reactions (NDA reactions) of 2-nitrosopyridine with various dienes are presented. The [CuPF(6)(MeCN)(4)]/Walphos-CF(3) catalyst system is best suited to catalyze the NDA reaction of various dienes by using 2-nitrosopyridine as a dienophile. In most of the cases studied, cycloadducts are obtained in quantitative yield with very good to excellent enantioselectivities. Based on DFT calculations, a model to explain the stereochemical outcome of the NDA reaction is presented. Finally, an efficient short synthesis of (-)-peracetylated conduramine A-1 by applying the enantioselective NDA reaction as a key step is described.
Jana
Chandan Kumar
CK
NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Correnstrasse 40, 48149 Münster, Germany.
Grimme
Stefan
S
Studer
Armido
A