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Download fileCatalytic Enantio- and Diastereoselective Cyclopropanation of 2‑Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers
journal contribution
posted on 2019-08-29, 19:03 authored by Xinxin Shao, Steven J. MalcolmsonWe report the catalytic
enantio- and diastereoselective preparation
of aminocyclopropanes by the cyclopropanation of terminal and (Z)-internal 2-azadienes with donor/acceptor carbenes derived
from α-diazoesters. The resulting cyclopropanes bear quaternary
carbon stereogenic centers vicinal to the amino-substituted carbon
and are formed as a single diastereomer in up to 99:1 er and 97% yield
with 0.5 mol % of Rh2(DOSP)4 and only 1.5 equiv
of the diazo reagent. Transformations with internal azadienes afford
cyclopropanes with three contiguous stereogenic centers.
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α- diazoesterscyclopropanationmol0.5Rh 2diastereoselective preparationDOSPTransformationamino-substituted carbonaminocyclopropaneDiastereoselective CyclopropanationCatalytic Enantioenantioterminal1.5 equivquaternary carbon stereogenic centers vicinalSynthesidiastereomerdonor2- azadienesAzadieneAminocyclopropanes Bearing Quaternary Carbon Stereogenic Centersstereogenic centersdiazo reagentcarbene