Exploration of the enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters |
| |
Authors: | Paul Tapas Malachowski William P Lee Jisun |
| |
Affiliation: | Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, USA. |
| |
Abstract: | Quaternary stereocenters on a 2-cyclohexen-1-one ring are synthesized with good to excellent levels of enantioselectivity. The quaternary stereocenter is created through a new synthetic sequence involving three reactions: the enantioselective Birch reduction-allylation, enol ether hydrolysis, and the Cope rearrangement. To illustrate the ability of the sequence to enantioselectively generate complex structures, a variety of substrates are described. Notably, the sequence works for the enantioselective generation of vicinal quaternary-tertiary stereocenters, the generation of congested arylic quaternary stereocenters, and hydroxyalkyl substituted quaternary stereocenters. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|