期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 22, 页码 7091-7094出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b04168
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资金
- Advanced Catalytic Transformation Program for Carbon Utilization
- Pharmaceutical Chemicals Co., Ltd
- Advance Electric Co., Inc.
- [23225002]
- Grants-in-Aid for Scientific Research [23225002] Funding Source: KAKEN
Highly diastereo- and enantioselective Mukaiyama aldol reaction catalyzed by a new chiral Bronsted acid, N-(perfluorooctanesulfonyl)-thiophosphoramide, is described. The perfluotooctyl substituent on the sulfonyl group of the catalyst plays an essential role in the stereoselection. The catalyst also allows the asymmetric Hosomi-Sakurai allylation, which has been considerably challenging due to the low reactivity of allylsilanes. (29)S1 and P-31 NMR monitoring reveals the characteristic feature of the thiophosphoramide catalyst, acting as a strong Bronsted acid even in the presence of excess silyl nudeophiles, which cannot be found in other related phosphoric acid analogues.
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