Asymmetric allylic alkylation of acyclic allylic ethers with organolithium reagents.
A highly efficient, regio- and enantioselective Cu(I)/phosphoramidite-catalyzed asymmetric allylic alkylation of allyl ethers with organolithium reagents is reported (see scheme). The use of organolithium reagents is essential for this catalytic C-C bond formation due to their compatibility with different Lewis acids. The versatility of allylic ethers under the copper-catalyzed reaction conditions with organolithium reagents is demonstrated in the shortest synthesis of (S)-Arundic acid.
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Manuel
M
Pérez
Martín
M
Fañanás-Mastral
Valentín
V
Hornillos
Alena
A
Rudolph
Pieter H
PH
Bos
Syuzanna R
SR
Harutyunyan
Ben L
BL
Feringa
D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D002210:Caprylates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000498:Allyl Compounds; D002210:Caprylates; D004987:Ethers; D007202:Indicators and Reagents; D018020:Lithium Compounds; C459360:ONO2506; D003300:Copper