Abstract
The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.
Original language | English |
---|---|
Pages (from-to) | 8713-8717 |
Number of pages | 5 |
Journal | Organic letters |
Volume | 21 |
Issue number | 21 |
DOIs | |
Publication status | Published - 1 Nov 2019 |
Funding
This work was financially supported by the National Natural Science Foundation of China (21572081, 21762024, and 21877055) and Natural Science Foundation of Jiangxi Province (20161ACB20005, 20171BCB23036, and 20171BAB203008). The Innovative Fund of Jiangxi Province to H.L. (YC2018-B031) was also appreciated. The authors thank the SURFsara for use of the Lisa.