Desymmetrizing oxetanes

Jianwei Sun and co-workers from the Hong Kong University of Science and Technology have reported in ACIE on a desymmetrization of oxetanes using a phosphoric acid catalyst.

ACIE paper

Madindoline from desymmetrization

Koichi Mikami and co-workers from Tokyo Institute of Technology have reported in JACS on a desymmetrization approach to access madindoline B.

JACS paper

Desymmetrizing a meso compound

Pauline Chiu and co-workers from the University of Hong Kong have published in Tetrahedron Letters on a desymmetrization of a meso compound to form a five membered ring with modest ee (50% ee).

TL paper

Hodgkinsine B synthesis

My first look at the authors on this paper made me think: “Whoa Woodward’s back from the dead” but I realized the middle initial is different.

ACIEE paper

Desymmetrize this

Keiji Maruoka and co-workers from Kyoto University have reported in JACS on a desymmetrization process of a cyclohexanone using an alphadiazoacetate reagent to afford seven membered rings.

JACS paper

LFER Analysis of a Desymmetrization Reaction

One of the classical ways to study a reaction’s mechanism is to use the linear free energy relationship analysis – Scott Miller (Yale) and Matthew Sigman (Utah) have published in Organic Letters on their LFER analysis of a desymmetrization reaction using a diarylmethane-bisphenol substrate with the peptide catalyst that Miller has been using to desymmetrize meso starting materials.  The reaction in this paper is to selectively acetylate one of the phenols over the other to yield chiral products – the third substituent on the methane was varied with sterically different groups.

OL paper