Abstract
The rhodium-catalyzed, directed catalytic asymmetric hydroboration of γ,δ-unsaturated amides affords a direct route to chiral acyclic secondary γ-borylated carbonyl derivatives in high enantiomeric purity. In contrast to a similar β-borylated amide derivative, the γ-borylated amide undergoes Suzuki-Miyaura cross-coupling with stereoretention. The utility of the boronic ester products is further illustrated by other stereospecific C-B bond transformations leading to γ-amino acid derivatives, 1,4-amino alcohols, and 5-substituted-γ-lactone and γ-lactam ring systems.
Original language | English (US) |
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Pages (from-to) | 4511-4516 |
Number of pages | 6 |
Journal | Chemical Science |
Volume | 8 |
Issue number | 6 |
DOIs | |
State | Published - 2017 |
ASJC Scopus subject areas
- Chemistry(all)