期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 38, 页码 13613-13618出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602347
关键词
cycloisomerization; cyclopropanation; density functional calculations; gold; rearrangement
资金
- MINECO [SEV-2013-0319, CTQ2013-42106-P]
- MEC
- European Research Council [321066]
- AGAUR [2014 SGR 818]
- Marie Curie program [658256-MSCA-IF-EF-ST]
- ICIQ Foundation
1,6-Enynes bearing OR groups at the propargyl position generate ,-unsaturated gold(I)-carbenes/ gold(I) stabilized allyl cations that can be trapped by alkenes to form cyclopropanes or 1,3-diketones to give products of -alkylation. The best migrating group is p-nitrophenyl ether, which leads to the corresponding products without racemization. Thus, an improved formal synthesis of (+)-schisanwilsonene A has been accomplished. The different competitive reaction pathways have been delineated computationally.
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