OChem Fun!

Every Saturday at 10:30am the Sharma Laboratory hosts a weekly literature meeting for graduate students and post-doctoral researchers from our own lab and other labs across the department to attend. To begin the meeting we work through a “Mechanism of the Week”. Following the problem solving session, a volunteer for the week will present a talk on any topic found within literature. Below are the mechanisms and links to powerpoint presentations! This page has recently undergone construction, so please return in the future for a larger listing!


 

February 2nd, 2019

An interesting synthesis of seven membered carbocycles from readily available chemical building blocks was reported in 1986. MeMgBr was added to the cyclopropane hemiketal, then the cyclohexane enolate (2 eq.) was added via cannula to the reaction. Please identify the mechanism of this transformation and provide a transition state of the key intermediate that explains the stereoselectivity and reactivity observed in this reaction

An interesting synthesis of seven membered carbocycles from readily available chemical building blocks was reported in 1986. MeMgBr was added to the cyclopropane hemiketal, then the cyclohexane enolate (2 eq.) was added via cannula to the reaction. Please identify the mechanism of this transformation and provide a transition state of the key intermediate that explains the stereoselectivity and reactivity observed in this reaction

SOLUTION

SOLUTION


January 26TH, 2019

In a classic thermal transformation the acyl azide above was heated in the presence of butanol to afford a 1:1 mixture of diastereomers. Later studies determined that the enantiomerically pure starting material above provides each diastereomer enatiomerically pure. Please provide a mechanism for this transformation while paying attention to the stereochemistry.

In a classic thermal transformation the acyl azide above was heated in the presence of butanol to afford a 1:1 mixture of diastereomers. Later studies determined that the enantiomerically pure starting material above provides each diastereomer enatiomerically pure. Please provide a mechanism for this transformation while paying attention to the stereochemistry.

SOLUTION

SOLUTION