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Archive for the ‘Ylides’ Category

Didehydrostemofoline formal synthesis

Posted by naturalproductman on October 2, 2012

Stephen Martin and co-workers have reported in ACIE on a formal synthesis of didehydrostemofoline.

alkaloid

ACIE paper

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

Acetylaranotin synthesis

Posted by naturalproductman on October 28, 2011

Sarah Reisman and co-workers have reported in JACS on a synthesis of acetylaranotin.

1,3-dipolar

JACS paper

Posted in Alkaloids, Cascade Reactions, Methodology, Total Synthesis, Transition Metal, Ylides | Leave a Comment »

Ir-catalyzed cascade

Posted by naturalproductman on July 5, 2011

Xingwei Li and co-workers at the Chinese Academy of Sciences have reported on the formation of azomethine ylides using nitron alkynes.

ir

ACIEE paper

Posted in Cascade Reactions, Diels-Alder, Iridium, Methodology, Named Reactions, Transition Metal, Ylides | Leave a Comment »

Olefination with an alkyne

Posted by naturalproductman on June 7, 2011

Kurt Gothelf and co-workers from Aarhus University have reported in Organic Letters on a beta-olefination process involving an alkynoate and an aldehyde in the presence of 1,3,5-triaza-7-phospha-adamantane (PTA).

beta-olefination

OL paper

Posted in Cascade Reactions, Methodology, Named Reactions, Wittig, Ylides | Leave a Comment »

Dimethylsulfonium Methylide Cascade

Posted by naturalproductman on February 12, 2011

If I were to tell you a dimethylsulfonium methylide were used as the reagent – you’d probably predict it to be a Corey-Chaykovsky reaction.  However, in this case reported by Philip Fuchs and colleague at Purdue, it is an SN2 prime addition followed by an elimination of dimethyl sulfide.

dimethyl sulfide

Chem Comm paper

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

Multi-Component Cascade

Posted by naturalproductman on January 21, 2011

Xian Huang and co-workers from Zhejiang University have published in Organic Letters on a multi-component coupling approach that takes advantage of an interesting way to form a phosphorous ylide – by addition of an alkyl lithium onto an alkynyl phosphine oxide.

phosphine

 

JOC paper

Posted in Cascade Reactions, Methodology, Ring forming, Ylides | Leave a Comment »

Oxonium Ylide Approach to Seven Membered Rings

Posted by naturalproductman on January 11, 2011

F. G. West and co-workers at the University of Alberta have published in Organic Letters on a copper catalyzed oxonium ylide generation.

daphnane

 

OL paper

Posted in Copper, Named Reactions, Transition Metal, Ylides | Leave a Comment »

1,3-Dipolar Cycloaddition Followed by Decarboxylation

Posted by naturalproductman on December 26, 2010

John Ryan and co-workers at the University of Melbourne have published in Organic Letters on a reaction which involves the 1,3-dipolar cycloaddition between an anhydride and a non-stabilized ylide followed by decarboxylation.

1,3-dipolar cycloaddition

 

OL paper

Posted in Cascade Reactions, Cycloaddition, Methodology, Pericyclic reactions, Ylides | Leave a Comment »

Rhodium catalyzed Oxonium Ylide

Posted by naturalproductman on November 17, 2010

Stephen Clark and co-workers from the University of Glasgow have reported in ACIEE on their syntheses of cladiellins using an oxonium ylide approach via a rhodium dimer catalyst.

cladiellins

 

ACIEE paper

Posted in Carbene, Cascade Reactions, Methodology, Rhodium, Transition Metal, Ylides | Leave a Comment »

Epoxide and Oxetane Expansions

Posted by naturalproductman on August 21, 2010

Andrey Fokin and co-workers at Justus-Liebig University have published in the Journal of Organic Chemistry on a method to expand epoxides using a sulfur ylide.

epoxide expansion

JOC paper

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

 
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