de Jesús Cruzet al., Science 376 , 1224–1230 (2022) 10 June 2022 4of7
Fig. 3. Substrate scope of the crystallization-enabled doubly stereo-
convergent conjugate addition.Reaction conditions were as follows: cat.
A (20 mol %), alkylidene (0.200 mmol, 1.0 equiv, 1 M), EtNO 2 (0.600 mmol,
3.0 equiv), 2-Me-THF (0.200 ml), 23°C, 48 hours. Yields refer to isolated
yields. The diastereomeric ratio values were determined by^1 HNMR
spectroscopic analysis of the solidobtained by filtration of the crude
reaction mixture. The er values of the solids after filtration were determined
by high-performance liquid chromatographic analysis using a chiral station-
ary phase. *Reaction performed in Et 2 Oassolvent.†Reaction performed with
1-nitropropane (0.600 mmol, 3.0 equiv).‡Reaction performed with MTBE
(0.2ml,1.0M).§Reactionperformedwith nitroethanol (0.600 mmol, 3.0
equiv). ¶Reaction performed with ethyl nitroacetate (0.600 mmol, 3.0 equiv).
#Reaction performed with (nitromethyl)benzene (0.600 mmol, 3.0 equiv).
**Crystallization observed after 96 hours.RESEARCH | REPORT