Asymmetric Bronsted Acid Catalyzed Nucleophilic Addition to in situ Generated Chiral N-Acyliminium Ions

被引：85

作者：

Rueping, Magnus ^{[1
]}

Nachtsheim, Boris J. ^{[2
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

[2] Harvard Univ, Sch Med, Dept Biol Chem & Mol Pharmacol, Boston, MA 02115 USA

来源：

SYNLETT | 2010年 / 01期

关键词：

organocatalysis; nucleophilic substitution; protonation; amino acid; quaternary stereocenter; X-RAY-CRYSTAL; TRANSFER HYDROGENATION; ENANTIOSELECTIVE REDUCTION; ORGANOCATALYTIC REDUCTION; NMR-SOLUTION; METAL-FREE; CYCLIZATION; ALDEHYDES;

D O I：

10.1055/s-0029-1218539

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new enantioselective Bronsted acid catalyzed nucleophilic Substitution of gamma-hydroxylactams with indole is presented. The reaction proceeds via an intermediary N-acyliminium ion and provides disubstituted gamma-lactams in good yields and with high enantioselectivities.

引用

页码：119 / 122

页数：4

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