期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 50, 页码 15957-15963出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b11273
关键词
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资金
- ACT-C
- JST
- [23225002]
- Grants-in-Aid for Scientific Research [23225002] Funding Source: KAKEN
The nitroso Diels-Alder (NDA) reaction is an attractive strategy for the synesis of 3,6-dihydro-1,2-oxazines and 1-arnino-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 narcidasine were accomplished.
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