Direct Enantioselective Bronsted Acid Catalyzed N-Acyliminium Cyclization Cascades of Tryptamines and Ketoacids

被引：123

作者：

Holloway, Chloe A. ^{[2
]}

Muratore, Michael E. ^{[1
]}

Storer, R. Ian ^{[3
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[3] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

ACCESS;

D O I：

10.1021/ol101651t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with gamma- and delta-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).

引用

页码：4720 / 4723

页数：4

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