Premium
Asymmetric Synthesis of α‐Acyl‐γ‐butyrolactones Possessing All‐Carbon Quaternary Stereocenters by Phase‐Transfer‐Catalyzed Alkylation
Author(s) -
Ooi Takashi,
Miki Takashi,
Fukumoto Kazuhiro,
Maruoka Keiji
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606064
Subject(s) - stereocenter , alkylation , chemistry , enantioselective synthesis , catalysis , bromide , ammonium , quaternary carbon , organic chemistry , combinatorial chemistry
The enantioselective construction of all‐carbon quaternary stereocenters on α‐acyl‐γ‐butyrolactones has been achieved by the N ‐spiro chiral quaternary ammonium bromide 1 ‐catalyzed alkylation under mild phase‐transfer conditions. The resulting α‐alkylated keto lactones serve as valuable chiral building blocks in organic synthesis as clearly demonstrated by the facile conversion to optically active α,α‐dialkyl‐α‐amino acid derivatives via Schmidt rearrangement.