NMR spectroscopic investigations of mixed aggregates underlying highly enantioselective 1, 2-additions of lithium cyclopropylacetylide to quinazolinones

RL Parsons, JM Fortunak, RL Dorow…

Index: Kauffman, Goss S.; Harris, Gregory D.; Dorow, Roberta L.; Stone, Benjamin R. P.; Parsons Jr., Rodney L.; Pesti, Jaan A.; Magnus, Nicholas A.; Fortunak, Joseph M.; Confalone, Pat N.; Nugent, William A. Organic Letters, 2000 , vol. 2, # 20 p. 3119 - 3121

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Citation Number: 41

Abstract

The solution structures of mixed aggregates derived from lithium alkoxides and lithium acetylides were investigated as part of a program to develop practical syntheses of quinazolinone-based nonnucleoside reverse transcriptase inhibitors. Low-temperature 6Li, 13C, and 15N NMR spectroscopies reveal that mixtures of lithium cyclopropylacetylide (RCCLi), a (+)-carene-derived amino alkoxide (R* OLi), and lithium hexamethyldisilazide ( ...