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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals
Rayala Naveen Kumar1, Seongmin Lee1
1The Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USA.
Abstract:
The hypervalent iodine-mediated formation of steroidal 5/5-spiroiminals and 5/5-spiroaminals from steroidal amines is presented. Under the influence of excess PhI(OAc)2 and iodine in acetonitrile at 0 °C, steroidal amines smoothly underwent cyclization to give a mixture of 5/5-spiroiminals and 5/5-spiroaminals. This reaction represents the first example of a C-H-activation-mediated formation of a spiroiminal. Presumably, the formation of 5/5-spiroiminals occurs through aminyl radical-mediated cyclization followed by amine-to-imine oxidation.
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