Convenient transformation of optically active nitroalkanes into chiral aldoximes and nitriles

被引:132
作者
Czekelius, C [1 ]
Carreira, EM [1 ]
机构
[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
chirality; nitro compounds; oximes; reduction; synthetic methods;
D O I
10.1002/anie.200461879
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An environmentally friendly reaction that excludes the potential contamination of the products by metal impurities is reported. In this reaction, optically active aldoximes and nitriles are prepared from chiral nitroalkanes (see scheme). The methodology described expands the possibilities available for the conversion of nitroalkanes into valuable targets.
引用
收藏
页码:612 / 615
页数:4
相关论文
共 65 条
[21]   Enantioselective rare-earth catalyzed quinone Diels-Alder reactions [J].
Evans, DA ;
Wu, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10162-10163
[22]   Stereochemically rich pentaketides from bis(isoxazolines): A general strategy for efficient polyketide synthesis [J].
Fader, LD ;
Carreira, EM .
ORGANIC LETTERS, 2004, 6 (14) :2485-2488
[23]  
Feuer H., 1990, In Nitro Compounds: Recent Advances in Synthesis and Chemistry
[24]   FLUORINATED AROMATIC AMINO ACIDS .1. O, M, AND P-TRIFLUOROMETHYLPHENYLALANINES [J].
FILLER, R ;
NOVAR, H .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (05) :733-736
[25]   Asymmetric 1,3-dipolar cycloaddition reactions [J].
Gothelf, KV ;
Jorgensen, KA .
CHEMICAL REVIEWS, 1998, 98 (02) :863-909
[26]   A PROPOSED MECHANISM OF THE ALKYLATION OF BENZYL HALIDES WITH NITRO PARAFFIN SALTS [J].
HASS, HB ;
BENDER, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (10) :3482-3485
[27]   THE REACTION OF BENZYL HALIDES WITH THE SODIUM SALT OF 2-NITROPROPANE - A GENERAL SYNTHESIS OF SUBSTITUTED BENZALDEHYDES [J].
HASS, HB ;
BENDER, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (05) :1767-1769
[28]   ALIPHATIC DIAZO COMPOUNDS - INVESTIGATION OF ALPHA-DIAZO-GAMMA,GAMMA,GAMMA-TRIPHENYLPROPANE, IN RELATION TO MOLECULAR REARRANGEMENTS AND STABILITY [J].
HELLERMAN, L ;
GARNER, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (05) :819-823
[29]  
Hudlicky M., 1984, Reductions in organic chemistry
[30]  
Hughes CC, 2002, ANGEW CHEM INT EDIT, V41, P4556, DOI 10.1002/1521-3773(20021202)41:23<4556::AID-ANIE4556>3.0.CO