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
收藏
页码：119 / 122
页数：4
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