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Archive for the ‘Cascade Reactions’ Category

multiple reactions back to back (to back) in one go

[4+2] with diazo esters

Posted by naturalproductman on February 8, 2016

Michael Doyle and co-workers at UT San Antonio have reported in JACS on the first Diels-Alder example involving a diazoester dienophile.

DOYLE jacs 2016

JACS paper

Posted in Cascade Reactions, Mechanistic, Methodology | Leave a Comment »

Jungermannenones B and C synthesis

Posted by naturalproductman on January 29, 2016

Xiaoguang Lei and co-workers from Peking University have reported in ACIE on the synthesis of jungermannenones B and C.

 

ACIE paper

Posted in Cascade Reactions, Methodology, Radical Chemistry, Total Synthesis | Leave a Comment »

3 Diels-Alder reactions in 1 go

Posted by naturalproductman on January 29, 2016

Michael Sherburn and co-workers from the Australian National University reported in JOC on a Diels-Alder cascade sequence.

DIELS ALDER CASCADE 01.29.2016.gif

JOC paper

 

Here’s an interesting related ACIE paper by the same group.

Posted in Cascade Reactions, Diels-Alder, Methodology, Named Reactions | Leave a Comment »

2 Reagents, 2 mechanisms, same product

Posted by naturalproductman on January 28, 2016

Srinivasan Chandrasekaran and colleague at the Indian Institute of Science have reported in Tetrahedron on a mechanistically interesting transformation involving a geminal aminooxygenation of a vinyl arene. Two different reaction conditions were identified: one with m-CPBA, the other with a hypervalent iodine reagent. The former underwent a deuterium shift on the gem-dideuterated-styrene starting material and the latter does not.

01.28.2016 naturalproductman.gif

Tetrahedron paper

Posted in Cascade Reactions, Hypervalent Iodine, Mechanistic, Methodology | Leave a Comment »

Expect the unexpected – allylic alcohols from epoxides

Posted by naturalproductman on January 27, 2016

Margaret Brimble and co-workers from the University of Auckland have reported in Organic Letters on a cobalt-catalyzed conversion of an epoxide to an allylic alcohol using the Corey-Chaykovsky reagent.

 

OL paper

Posted in Cascade Reactions, Cobalt, Methodology, Transition Metal | Leave a Comment »

Fusarisetin A synthesis

Posted by naturalproductman on January 27, 2016

Yandong Zhang and co-workers at Xiamen University have reported in Organic Letters on a synthesis of fusarisetin A using a one pot intramolecular Diels-Alder/Mukaiyama aldol reaction cascade sequence.

OL paper

Posted in Cascade Reactions, Diels-Alder, Named Reactions, One pot, Total Synthesis | Leave a Comment »

From carboxylic acid to ketone

Posted by naturalproductman on January 26, 2016

Peter Schreiner and co-workers from Justus-Liebig University have reported in ACIE on an asymmetric Dakin-West reaction. I am reminded of a similar transformation from carboxylic acid chlorides to trifluoroketones reported by Samir Zard’s group. From my own experience, the Zard reaction also works with just a carboxylic acid as the starting material (except, as pointed out – is not an asymmetric reaction).

 

ACIE paper

Posted in Asymmetric, Cascade Reactions, Dakin-West, Methodology, Named Reactions | 2 Comments »

Back to Back Method Papers: Allenamide + Aldehyde = alpha-Alkylation

Posted by naturalproductman on January 22, 2016

Fernando Lopez and co-workers at Universidad de Santiago de Compostela have reported in Chemical Communications on a gold/organocatalyst-cocatalyzed alpha alkylation of aldehydes. Interestingly Jose Gonzalez and co-workers at Universidad de Oviedo also reported in Chem Comm on a gold/organocatalyst reaction.

 

Chem Comm paper

 

Chem Comm paper 2

Posted in Allenes, Asymmetric, Cascade Reactions, Cooperative Catalysis, Gold, Methodology, Organocatalytic, Transition Metal | Leave a Comment »

Hetero-Diels-Alder/Oxy-Michael cascade

Posted by naturalproductman on January 22, 2016

John Gao and co-workers from UT San Antonio have reported in ACIE on the use of modularly designed organocatalysts (MDO) to effect a hetero-Diels-Alder/oxy-Michael cascade reaction.

 

ACIE paper

Posted in Cascade Reactions, Diels-Alder, Kinetic resolution, Methodology, Named Reactions, Organocatalytic, Oxy-Michael | Leave a Comment »

Access to 7-membered rings from lactams

Posted by naturalproductman on January 22, 2016

Scott Sieburth and co-workers from Temple University reported in ACIE on an interesting transformation converting a delta-lactam to a cycloheptanone ring.

 

ACIE paper

Posted in Cascade Reactions, Kulinkovich-de Meijere, Named Reactions, Titanium, Transition Metal | Leave a Comment »

 
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