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Archive for the ‘Hypervalent Iodine’ Category

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 »

ACIE Journals of Interest 11/24/2015

Posted by naturalproductman on November 24, 2015

Hao Xu’s lab in University of Georgia have reported on an iron-catalyzed diazidation of olefins.

Dorian Didier’s lab from LMU Munich reported on an interesting one-pot reaction.

Xiaoguang Lei’s lab from Peking University reported on the structural revision of aspergillomarasmine A.

Kilian Muniz’s lab from ICIQ reported on a hypervalent iodine approach to form 1,2-diacetates from olefins, asymmetrically.

NATURALPRODUCTMAN11.24.2015

Posted in Cascade Reactions, Hypervalent Iodine, Methodology, Structural Reassignment, Total Synthesis | Leave a Comment »

Radical cascade using hypervalent iodine

Posted by naturalproductman on October 1, 2015

Xin-Hua Duan and co-workers from Xi’an Jiaotong University have reported in Organic Letters on a hypervalent iodine approach to accessing alkynylated ketones.
alkylation

OL paper

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

Syn-1,3-carbonate access

Posted by naturalproductman on May 28, 2015

Matthew Gaunt and colleague at the University of Cambridge have reported in ACIE on a method for the synthesis of syn-1,3-carbonates.

Cu

ACIE paper

Posted in Copper, Hypervalent Iodine, Methodology, Transition Metal | Leave a Comment »

Hypervalent iodine towards lactams

Posted by naturalproductman on May 2, 2015

Antonio Herrera and co-workers from CSIC have reported in Organic Letters on a hypervalent iodine approach to access lactams from linear precursors.

OL paper

Posted in Hofmann–Löffler–Freytag-type, Hypervalent Iodine, Methodology, Named Reactions | Leave a Comment »

Trifluoromethylation with hypervalent iodine

Posted by naturalproductman on April 12, 2015

Mikiko Sodeoka and co-workers from RIKEN have reported in JACS on a aminotrifluoromethylation of olefins using a hypervalent iodine reagent.
iodine

JACS paper

Posted in Hypervalent Iodine, Methodology | Leave a Comment »

Difluorination using hypervalent iodine

Posted by naturalproductman on November 10, 2014

Kálmán J. Szabó and co-workers from Stockholm University have reported in ACIE on a difluorination of styrene using a hypervalent iodide reagent.

fluorination
ACIE paper

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

Phenolic coupling for morphine

Posted by naturalproductman on November 10, 2014

Matthew Gaunt and co-workers from the University of Cambridge have reported in ACIE on the formal synthesis of morphine through an oxidative phenolic coupling.

morphine

ACIE paper

Posted in Alkaloids, Cascade Reactions, Hypervalent Iodine, Methodology, Total Synthesis | Leave a Comment »

Aspeverin synthesis

Posted by naturalproductman on August 30, 2014

Adam Levinson at Sloan Kettering has reported in Organic Letters on the synthesis of aspeverin. Interestingly, Danishefsky was acknowledged for the mentorship but not included in the authors list. I wonder if this is a new kind of way to publish.

aspeverin

OL paper

Posted in Alkaloids, Hypervalent Iodine, Methodology, Total Synthesis | 3 Comments »

Hypervalent iodine promoted aryl shift

Posted by naturalproductman on May 10, 2013

Thomas Wirth and co-workers at Cardiff University have reported in ACIE on a hypervalent iodine reagent promoted migration of an aryl group.

iodine

ACIE paper

Posted in Asymmetric, Hypervalent Iodine, Methodology | Leave a Comment »

 
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