Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 42, Pages 13240-13243Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606195
Keywords
allenes; cycloaddition; heterocycles; rhodium; synthetic methods
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Funding
- NIH [1R01GM111412-01, RR08389-01, P41GM103399, S10RR08438, S10RR029220]
- NSF [1254397, CHE-9208463, CHE-9629688, BIR-0214394]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1254397] Funding Source: National Science Foundation
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A tandem allene aziridination/[4+3]/reduction sequence converts simple homoallenic sulfamates into densely functionalized aminated cycloheptenes, where the relative stereochemistry at five contiguous asymmetric centers can be controlled through the choice of the solvent and the reductant. The products resulting from this chemistry can be readily transformed into complex molecular scaffolds which contain up to seven contiguous stereocenters.
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