(Equation Presented) Addition of Zn(n-Bu3Sn)2 to prochiral aldehydes affords anti-α,β-dialkoxy- and anti-α-alkoxy-β-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de), syn-lsomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(l)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry