Bifunctional homoallylic carbamates from chiral silane additions to in situ generated N-acyl iminium ions.
Homoallylic carbamates bearing an α,β-unsaturated ester or an allylic carbonate were generated respectively utilizing novel chiral silanes through Lewis acid promoted asymmetric aminocrotylation. Those bifunctional building blocks could further undergo Michael addition or cyclization to selectively form functionalized lactams, azetidines, and tetrahydropyrimidinones.
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University , Boston, Massachusetts 02215, United States.
Jie
J
Wu
Kai-Cheng
KC
Zhu
Ping-Wei
PW
Yuan
James S
JS
Panek
D002219:Carbamates / Q000737:chemistry*; D003500:Cyclization; D007477:Ions / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D002219:Carbamates; D007477:Ions; D058116:Lewis Acids; D012821:Silanes