Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 52, Pages 16136-16140Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609330
Keywords
cyclohexanes; donor-acceptor cyclobutanes; enantioselective catalysis; N-heterocyclic carbenes; organocatalysis
Categories
Funding
- Australian Research Council [DP150101522, FT110100319]
- Australian Research Council [FT110100319] Funding Source: Australian Research Council
Ask authors/readers for more resources
Herein we report the enantioselective (4+2) annulation of donor-acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl -lactones (25 examples) in excellent chemical yield (most 90%) and stereochemical integrity (all >20:1 d.r., most 97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available
Share Paper
