Journal
PURE AND APPLIED CHEMISTRY
Volume 82, Issue 7, Pages 1353-1364Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1351/PAC-CON-09-12-09
Keywords
catalysis; cycloadditions; indolizidines; quinolizidines; rhodium
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Funding
- NIGMS NIH HHS [R01 GM080442, R01 GM080442-01A1] Funding Source: Medline
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The discovery and development of the asymmetric rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl isocyanates and exogenous alkynes to form indolizinone and quinolizinone scaffolds is described. This methodology has been expanded to include substituted alkenes and dienes, a variety of sterically and electronically diverse alkynes, and carbodiimides in place of the isocyanate. Through X-ray analysis of Rh(cod)/phosphoramidite complexes additives that modify the enantio-determining step, and other experimental data, a mechanism has been proposed that explains lactam, vinylogous amide, and pyridone products and the factors governing their formation. Finally, we have applied this methodology to the synthesis of (+)-lasubine II and (-)-209D.
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