The Synthesis of Long??Chain α??Alkyl?螃漫?Hydroxy Esters Using Allylic Halides in a Fráter–Seebach Alkylation

…, SH Chee, BL Stocker, MSM Timmer

Index: Khan, Ashna A.; Chee, Stephanie H.; Stocker, Bridget L.; Timmer, Mattie S. M. European Journal of Organic Chemistry, 2012 , # 5 p. 995 - 1002

Full Text: HTML

Citation Number: 3

Abstract

Abstract The Fráter–Seebach alkylation is a highly efficient means to diastereoselectively introduce α-substituents to chiral β-hydroxy esters, however, the yields of reactions in which longer chain alkyl halides are used can be disappointing. To provide a more robust protocol for the alkylation of β-hydroxy esters, we prepared a variety of long-chain allylic iodides with the view that the greater reactivity of the allylic system would lead to enhanced efficiency. ...