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Archive for the ‘Desymmetrization’ Category

Desymmetrizing oxetanes

Posted by naturalproductman on May 21, 2013

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.

desymmetrization

ACIE paper

Posted in Asymmetric, Desymmetrization, Methodology | Leave a Comment »

Madindoline from desymmetrization

Posted by naturalproductman on June 13, 2012

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

desymmetrization

JACS paper

Posted in Alkaloids, Asymmetric, Cascade Reactions, Copper, Desymmetrization, Methodology, Transition Metal | Leave a Comment »

Desymmetrizing a meso compound

Posted by naturalproductman on November 12, 2011

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).

50%

TL paper

Posted in C2-Symmetric, Carbene, Copper, Desymmetrization, Methodology, Transition Metal | Leave a Comment »

Hodgkinsine B synthesis

Posted by naturalproductman on August 24, 2011

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.

alkaloid

ACIEE paper

Posted in Alkaloids, Asymmetric, Desymmetrization, Methodology, Palladium, Transition Metal | 1 Comment »

Desymmetrize this

Posted by naturalproductman on May 23, 2011

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.

binol

JACS paper

Posted in Asymmetric, Carbene, Cascade Reactions, Desymmetrization, Methodology, Ring expansion, Ring Opening | Leave a Comment »

LFER Analysis of a Desymmetrization Reaction

Posted by naturalproductman on August 12, 2010

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.

ee

OL paper

Posted in Asymmetric, Desymmetrization, Mechanistic, Methodology, Organocatalytic | Leave a Comment »

 
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