jo061205e_si_001.pdf (399.51 kB)
(S,S)-(+)-Pseudoephedrine as Chiral Auxiliary in Asymmetric Conjugate Addition and Tandem Conjugate Addition/α-Alkylation Reactions
journal contribution
posted on 2006-09-29, 00:00 authored by Efraim Reyes, Jose L. Vicario, Luisa Carrillo, Dolores Badía, Uxue Uria, Ainara IzaOrganolithium reagents undergo highly regio- and diastereoselective 1,4-addition to (S,S)-(+)-pseudoephedrine enamides furnishing the corresponding β-alkyl-substituted adducts in excellent yields and
diastereoselectivities. In addition, the intermediate lithium enolates generated after the conjugate addition
step undergo a highly diastereoselective alkylation reaction, furnishing α,β-dialkyl-substituted amides in
high yields. The obtained adducts have been converted into chiral nonracemic β-alkyl- and α,β-dialkyl-substituted carboxylic acids and γ-alkyl- and β,γ-dialkyl-substituted alcohols using very simple and high-yielding procedures.