Fig. 2 Nickel-catalyzed asymmetric synthesis of alkylboronate esters. (A and B) Variation in the coupling partners. The ee was determined by chiral high-performance liquid chromatography after oxidation to the alcohol. The yield was determined by isolation after chromatographic purification. (C) Functional-group compatibility. (D) Comparison of the enantioselectivity-determining step when using a chiral auxiliary versus a chiral catalyst. All data represent the average of two experiments. *α-iodoboronate was used. †Reaction temperature, 10°C. ‡Catalyst loading, 12% NiBr2•diglyme and 16% L*. TBS, tert-butyldimethylsilyl; Ac, acetyl; Ph, phenyl; Boc, t-butoxycarbonyl.
Fig. 4 Enantioenriched alkylboronate esters as versatile intermediates. The alkylboronate compounds are converted to diverse families of organic molecules through C–C, C–N, C–O, and C–halogen bond formation. NBS, N-bromosuccinimide; LDA, lithium diisopropylamide; TBAF, tetrabutylammonium fluoride; ArLi, [3,5-bis(trifluoromethyl)phenyl]lithium; NIS, N-iodosuccinimide.
Supplementary Materials
www.sciencemag.org/content/354/6317/1265/suppl/DC1
Materials and Methods
Supplementary Text
Tables S1 to S7
Spectral Data
References (27–38)
Additional Files
- A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters
Jens Schmidt, Junwon Choi, Albert Tianxiang Liu, Martin Slusarczyk, Gregory C. Fu
Materials/Methods, Supplementary Text, Tables, Figures, and/or References
- Materials and Methods
- Supplementary Text
- Tables S1 to S7
- Spectral Data
- References
