期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 8, 页码 3414-3426出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo5001737
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资金
- ANR [BS07-005-01]
A catalytic 1,3-dipolar cycloaddition between carboalkoxy ketonitrones and methacrolein under the effect of chiral ruthenium Lewis acid (R,R-1) was developed with high regio-, diastereo-, and enantiocontrol. The diastereochemical outcome of the cyclo addition reaction is marked by a significant solvent effect, and a divergent endo or exo control can be tuned by an appropriate choice of both the solvent and the N- and O-substituents of the ketonitrone. A rationale of the solvent effect, based on the computational study of the interactions between the methacrolein-Ru complex and its counteranion (SbF6-), is proposed to explain the selectivities obtained.
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