N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions
N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions
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DOI：
10.1021/ol0257981
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发表时间：
2002-05-16
期刊：
影响因子：
5.2
通讯作者：
Renaud, P
中科院分区：
文献类型：
--
作者：
Corminboeuf, O;Renaud, P
[图解]研究了N-烷氧基丙烯酰胺作为Lewis酸催化的Diels-Alder反应的底物。用由三异丁基铝和2，2-二甲基-α，α，α‘，α’-四-1-萘基-TADDOL(1-NaphtTADDOL)制备的非常简单的手性Lewis酸，对映体选择性高达92%ee。由乙二锌和1，1‘-二-2-萘酚(BINOL)容易制备的山本锌-BINOL的使用效率更高，对映体选择性可达96%ee。
[GRAPHICS]The use of N-alkoxyacrylamides as substrates for Lewis acid catalyzed Diels-Alder reactions has been examined. Enantioselectivities up to 92% ee have been achieved using very simple chiral Lewis acids prepared from triisobutylaluminum and 2,2-dimethyl-alpha,alpha,alpha',alpha'-tetra-1-naphthalenyl-TADDOL (1-NaphtTADDOL). The use of Yamamoto's Zn-BINOL, easily prepared from Et2Zn and 1,1'-bi-2-naphthol (BINOL), proved to be even more efficient, and enantioselectivities up to 96% ee were achieved.