Organocatalytic Asymmetric Hydrophosphonylation/Mannich Reactions Using Thiourea, Cinchona and Bronsted Acid Catalysts

被引：63

作者：

Bhadury, Pinaki S. ^{[1
]}

Li, Hu ^{[1
]}

机构：

[1] Guizhou Univ, Ctr Res & Dev Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China

来源：

SYNLETT | 2012年 / 08期

关键词：

chirality; enantioselectivity; diastereoselectivity; organocatalysts; Bronsted acids; absolute configuration; ALPHA-AMINO PHOSPHONATES; DIASTEREOSELECTIVE MANNICH REACTIONS; PERFORMANCE-LIQUID-CHROMATOGRAPHY; FRIEDEL-CRAFTS REACTION; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ANTIVIRAL ACTIVITIES; ANTIFUNGAL ACTIVITY; CONJUGATE ADDITION; AMINOPHOSPHONATE DERIVATIVES;

D O I：

10.1055/s-0031-1290193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This account summarizes the results of recent studies conducted in our group on the development of chiral thiourea/cinchona and Bronsted acid derived bifunctional organocatalysts. Selected asymmetric organocatalytic transformations were targeted to obtain enantioenriched bioactive products. Special emphasis was placed on the preparation of environmentally friendly anti-plant viral agents such as enantiomerically enriched alpha-aminophosphonates and methods to assess the enantiomeric purity of these products on selected chiral stationary phases. The review also tries to delineate the underlying mechanism of various asymmetric transformations by BINOL-phosphoric acid-induced activation of imines and to make unambiguous assignments of the absolute configuration of alpha-aminophosphonates obtained from organocatalytic hydrophosphonylation of pregenerated and in situ generated imines.

引用

页码：1108 / 1131

页数：24

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