- Iodine-Promoted Semmler–Wolff Reactions: Step-Economic Access to meta-Substituted Primary Anilines via Aromatization
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An atom- and step-economic access to an array of unprotected meta-substituted primary anilines was disclosed using the Semmler–Wolff reaction, promoted by molecular iodine. Therein, noble metal catalysts and inert atmosphere are unnecessary while the forcing reaction conditions and the lengthy synthesis can be avoided. The synthetic utility of this approach is evident in the de novo syntheses of three bioactive molecules with good total yields.
- Wang, Shi-Ke,You, Xia,Zhao, Da-Yuan,Mou, Neng-Jie,Luo, Qun-Li
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p. 11757 - 11760
(2017/09/07)
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- Experimental studies on the selective β-c-h halogenation of enones
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Here we describe the realization of a one-pot protocol for the β-C-H halogenation of cyclic enones via umpolung of the β-carbon. The developed method includes hydrazone formation and selective β-halogenation (bromination, chlorination) with N-bromosuccini
- Huber, Tatjana,Kaiser, Daniel,Rickmeier, Jens,Magauer, Thomas
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p. 2281 - 2294
(2015/03/18)
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- Catalytic Enantioselective Nitroso Diels-Alder Reaction
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The nitroso Diels-Alder (NDA) reaction is an attractive strategy for the synthesis of 3,6-dihydro-1,2-oxazines and 1-amino-4-hydroxy-2-ene derivatives. Herein we report the Cu(I)-DTBM-Segphos catalyzed asymmetric intermolecular NDA reaction of variously substituted cyclic 1,3-dienes using highly reactive nitroso compounds derived from pyrimidine and pyridazine derivatives. In most of the cases studied, the cycloadducts were obtained in high yields (up to 99%) with very high regio-, diastereo-, and enantioselectivities (up to regioselectivity > 99:1, d.r. > 99:1, and >99% ee). As an application of this methodology, formal syntheses of conduramine A-1 and narciclasine were accomplished.
- Maji, Biplab,Yamamoto, Hisashi
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supporting information
p. 15957 - 15963
(2016/01/09)
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