Asymmetric Synthesis of a Quaternary Carbon Stereogenic Center by Organocatalysis Using a Primary Amino Acid and Its Salt

被引：7
|
作者：
Yoshida, Masanori [1 ]
机构：
[1] Natl Inst Technol KOSEN, Asahikawa Coll, Liberal Arts & Sci, 2-1-6,Shunkodai 2 Jo, Asahikawa, Hokkaido 0718142, Japan
来源：
CHEMICAL RECORD | 2023年 / 23卷 / 07期
关键词：
organocatalysis; quaternary carbon; enantioselective synthesis; alkylation; primary amino acid; ALPHA-BRANCHED ALDEHYDES; CATALYTIC ENANTIOSELECTIVE CONSTRUCTION; CHIRAL PHOSPHORUS LIGANDS; MICHAEL-ADDITION; ALLYLIC ALKYLATION; INDUCTION REACTIONS; SYNERGISTIC CATALYSIS; ALLYLATING REAGENTS; BETA-KETOESTERS; KETONES;
D O I：
10.1002/tcr.202200276
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
In this personal account, our recent developments on the asymmetric synthesis of a quaternary carbon stereogenic center by organocatalysis using a primary amino acid and its salt as a catalyst are described in three chapters: (1) conjugate addition to nitroalkenes and vinyl ketones, (2) nucleophilic addition to pi-allyl palladium complexes, and (3) nucleophilic substitution reactions with allyl and propargyl halides. By these methods, asymmetric alpha-allylation of alpha-branched aldehydes and ketones smoothly proceeded to give gamma-nitroaldehydes, ketoaldehydes, alpha-allylated aldehydes, and alpha-allylated beta-ketoesters possessing a quaternary carbon stereogenic center in good yields with high enantioselectivities.
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页数：15
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