133146-85-7Relevant articles and documents
Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters Catalyzed by Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B
Shim, Su Yong,Kim, Jae Yeon,Nam, Miso,Hwang, Geum-Sook,Ryu, Do Hyun
, p. 160 - 163 (2016)
Chiral oxazaborolidinium ion-catalyzed asymmetric cyclopropanation of α- or α,β-substituted acroleins with α-alkyl-α-diazoesters has been developed. With this methodology, chiral functionalized cyclopropanes containing a quaternary stereogenic center were obtained with high to excellent enantioselectivities (up to >99% ee). The synthetic utility of optically enriched functionalized cyclopropane was demonstrated in the first total synthesis of (+)-hamavellone B, which establishes the absolute configuration of natural (+)-hamavellone B.
Photochemical Alkene Isomerization for the Synthesis of Polysubstituted Furans and Pyrroles under Neutral Conditions
Walker, Johannes C. L.,Werrel, Simon,Donohoe, Timothy J.
supporting information, p. 13114 - 13118 (2019/10/22)
A photochemical approach to polysubstituted heterocycles using UV-induced alkene isomerization is described. The method allows for the synthesis of disubstituted furans and pyrroles under mild and neutral conditions and also provides access to a class of trisubstituted furans pertinent to natural-product synthesis. The method has broad functional-group tolerance and many richly decorated heterocycles have been prepared incorporating functional groups that are unstable under Br?nsted and Lewis acidic conditions.
Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence
Diehl, Julian,Brückner, Reinhard
supporting information, p. 278 - 286 (2017/01/24)
An established route to enantiomerically pure β-hydroxy ketones proceeds through the asymmetric hydrogenation of β-keto esters, an ester/amide exchange, and the use of the resulting β-hydroxy amide for the acylation of an organometallic compound. We shortened this route by showing that β-keto Weinreb amides are hydrogenated with up to 99 % ee in the presence of [Me2NH2]+{[RuCl(S)-BINAP]2(μ-Cl)3}–(0.5 mol-%) at room temp./5 bar. These Weinreb amides were prepared by seemingly obvious yet unprecedented condensations of lithiated N-methoxy-N-methylacetamide with carboxylic chlorides (51–87 % yield). The resulting β-hydroxy Weinreb amides were used for the acylation of organolithium and Grignard reagents. They thus gave enantiomerically pure β-hydroxy ketones (28 examples). A selection of these compounds gave anti-1,3-diols after another C=O bond hydrogenation, or syn-1,3-diols by a Narasaka–Prasad reduction.
