Stereocontrolled Formation of 1,2,4–Triol Products via Sequential Carbamoyl Transfer-Aldol-Tishchenko Reactions
Written by Alex Shterenberg
A. Shterenberg, P. Smirnov and I. Marek
The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and The Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa 32 000, Israel
The development of efficient methods for the synthesis of complex natural and unnatural molecules remains an enduring challenge in current organic chemistry particularly for the creation of several stereogenic centers in acyclic system in a single-pot operation.
In this lecture, I would like to describe our latest results for the creation of 3 (or even 4) new sp3 stereogenic centers as unique diastereoisomer via a "carbamoyl transfer" followed by a tandem aldol-Tishchenko reaction from simple starting material.
The diastereoselectivity, scope and limitations of this new concept will be discussed in the lecture.
