17229-30-0Relevant articles and documents
Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β-Lactams
Jang, Yujin,Johnson, J. Drake,Jung, Myunggi,Lindsay, Vincent N. G.,Poteat, Christopher M.,Williams, Rachel G.
, p. 18655 - 18661 (2020/08/21)
Cyclopropanone derivatives have long been considered unsustainable synthetic intermediates because of their extreme strain and kinetic instability. Reported here is the enantioselective synthesis of 1-sulfonylcyclopropanols, as stable yet powerful equivalents of the corresponding cyclopropanone derivatives, by α-hydroxylation of sulfonylcyclopropanes using a bis(silyl) peroxide as the electrophilic oxygen source. This work constitutes the first general approach to enantioenriched cyclopropanone derivatives. Both the electronic and steric nature of the sulfonyl moiety, which serves as a base-labile protecting group and confers crystallinity to these cyclopropanone precursors, were found to have a crucial impact on the rate of equilibration to the corresponding cyclopropanone. The utility of these cyclopropanone surrogates is demonstrated in a mild and stereospecific formal [3+1] cycloaddition with simple hydroxylamines, leading to the efficient formation of chiral β-lactam derivatives.
The chemistry of small ring compounds. Part 46. Reduction of 1-halocyclopropyl sulfides by thiolates
Jorritsma, R.,Steinberg, H.,Boer, Th. J. de
, p. 288 - 298 (2007/10/02)
The reaction of 1-halocyclopropyl sulfides with sodium alkanethiolates in protic or aprotic solvents leads to high yields of cyclopropyl sulfides, in which halogen has been replaced by hydrogen.The complementary oxidized product is, in most cases, the thioketone or thioaldehyde derived from the alkanethiolate.The reduction is unaffected by radical scavengers or by one-electron donors.Reaction kinetics indicate that the reduction proceeds via the 1-(alkylthio)cyclopropyl cation.A mechanism is discussed (Scheme 9) in which this ambident cation is attacked by thiolate on sulfur.In the intermediary sulfonium ylid an intramolecular hydrogen shift leads to the observed products.
