Lithiated Carbamates: Chiral Carbenoids for Iterative Homologation of Boranes and Boronic Esters
Journal Article
Aggarwal, Jake L. Stymiest, Guillaume Dutheuil, Adeem Mahmood and Varinder K. . 2007
Publication Work Type:
PhD
Publication Online URL:
Volume Number:
102
Pages:
1455–1456
Publication Abstract:
We have developed a process for the homologation of boranes and boronic esters using Hoppe-type lithiated carbamates which shows very broad substratescope. The Hoppe-type lithiated carbamates are effectively chiral carbenoids and are derived from the simplest of reagents: primary alcohols. The power of the methodology lies in its iterative use. Thus, through two cycles of the homologation process, either enantiomer of either diastereo-mer can be easily accessed through appropriate choice of thechiral diamine employed (()-sparteine 12 or (+)-11).Application of this versatile methodology in natural product synthesis is currently underway.
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