131671-65-3Relevant academic research and scientific papers
Soft Enolization of 3-Substituted Cycloalkanones Exhibits Significantly Improved Regiocontrol vs Hard Enolization Conditions
Dwulet, Natalie C.,Ramella, Vincenzo,Vanderwal, Christopher D.
supporting information, p. 9616 - 9619 (2021/12/17)
Soft enolization conditions are revealed to be markedly better than the typically applied hard enolization protocols for regioselective enoxysilane formation from unsymmetrical 3-substituted cycloalkanones. Five-, six-, and seven-membered cycloalkanones each with 3-methyl, 3-isopropyl, or 3-phenyl substituents were investigated, and in all but one case, regioselectivities were ≥11:1 for enolization away from the substituent. These results are complementary to the regiospecific enoxysilane formation derived from cycloalkenone conjugate addition/enolate silylation.
Regio- and enantio-selective enolisations of cyclic ketones using chiral lithium amide bases
Bambridge, Kimberley,Clark, Barry P.,Simpkins, Nigel S.
, p. 2535 - 2542 (2007/10/02)
Enolisations of 3-methylcyclohexanone 16, and of a trans-fused perhydroisoquinolone derivative 8, using several chiral lithium amide bases have been examined.In reactions involving a single enantiomer of the ketone 8, the use of a chiral base can result in enhancement or reversal of the normal regioselectivity of enolisation to give the enol silane derivatives 9 and 10, depending on the configuration of the base used.Similar matched and mismatched results are observed when (R)-3-methylcyclohexanone, (R)-16, is treated with either enantiomer of the chiral base 3.A new type of kinetic resolution, termed regiodivergent resolution, is observed when enolisation of the racemic ketones 8 or 16 is carried out using the chiral base 3.
