期刊
ORGANIC LETTERS
卷 23, 期 21, 页码 8214-8218出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02947
关键词
-
资金
- National Science Foundation [CHE1665208, CHE-2101153]
By substituting the benzyl groups of glucosyl imidate donors with trifluoromethyl, a substantial increase in 1,2-cis-selectivity can be achieved when activated with TMS-I in the presence of triphenylphosphine oxide. The stereoselectivity depends on the number of trifluoromethyl groups, leading to high 1,2-cis-selectivity with reactive alcohol acceptors.
Here, we demonstrate that substitution of the benzyl groups of glucosyl imidate donors with trifluoromethyl results in a substantial increase in 1,2-cis-selectivity when activated with TMS-I in the presence of triphenylphosphine oxide. Stereoselectivity is dependent on the number of trifluoromethyl groups (4-trifluoromethylbenzyl vs 3,5-bis-trifluoromethylbenzyl). Particularly encouraging is that we observe high 1,2-cis-selectivity with reactive alcohol acceptors.
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