Portal de Periódicos da CAPES

Acyclic Stereocontrol in the Ireland–Claisen Rearrangement of α‐Branched Esters

2007; Wiley; Volume: 46; Issue: 39 Linguagem: Inglês

10.1002/anie.200702142

1521-3773

Ying‐Chuan Qin, Craig E. Stivala, Armen Zakarian,

Asymmetric Synthesis and Catalysis

To overcome the limitation of the poor diastereoselectivity of the title reaction with α-branched esters, chiral amides were used to generate the enolate intermediates diastereoselectively. The desired rearrangement then took place with efficient transfer of chirality to give densely functionalized products with at least one quaternary stereocenter (see scheme; PMB, TBS, and TBDPS are protecting groups). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z702142_s.html or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.