Functionalized organolithiums are becoming more and more important as reagents in organic synthesis as methods for their preparation are expanded, and as the number of stereoselective reactions in which they participate grows. In the α-aminoorganolithium field, the so-called "unstabilized" species - those that are not chelated and not stabilized by re-sonance or a dipole-exhibit extraordinary configurational stability and undergo efficient reactions with a wide variety of electrophiles. They also undergo sigmatropic rearrangements if appropriately substituted. This chapter reviews the chemistry of these species. This review is dedicated, with warm regards, to Professor Dieter Seebach, on the occasion of his 60th birthday, and in recognition of his many contributions to the field of organic chemistry in general and organic synthesis in particular.
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Robert E. Gawley (1997) studied this question.