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Sequential epoxide fragmentation/radical cyclizations mediated by samarium(II) iodide

✍ Scribed by Gary A. Molander; Carlos del Pozo Losada


Book ID
108378983
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
900 KB
Volume
54
Category
Article
ISSN
0040-4020

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Reaction of cyclic g-cyanoketones with 3 equiv. of SmI 2 in the presence of t-BuOH as a proton source in HMPA-THF without photoirradiation gave the desired a-hydroxycycloalkanones along with overreduced ketones after hydrolysis. In the absence of t-BuOH, the formation of the overreduced ketones was