One-pot synthesis of polysubstituted pyrrolidines from aminonitriles

被引:36
作者
Meyer, N [1 ]
Werner, F [1 ]
Opatz, T [1 ]
机构
[1] Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany
来源
SYNTHESIS-STUTTGART | 2005年 / 06期
关键词
pyrrolidines; aminonitriles; Michael additions; reductions; combinatorial chemistry;
D O I
10.1055/s-2005-861838
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Aminonitriles with a mono- or unsubstituted amino group as well as alpha(alkylideneaminomitriles can be employed as easily accessible alpha-aminocarbanion equivalents. Their alpha-deprotonation yields stabilized carbanions, which undergo smooth 1,4-addition to alpha,beta-unsaturated carbonyl compounds. The resulting delta-keto-alpha-aminonitriles can be reductively cyclized to form polysubstituted pyrrolidines.
引用
收藏
页码:945 / 956
页数:12
相关论文
共 41 条
[11]   SYNTHESIS OF UNSTABILIZED LINEAR IMINES BY VACUUM GAS-SOLID REACTIONS [J].
GUILLEMIN, JC ;
DENIS, JM .
TETRAHEDRON, 1988, 44 (14) :4431-4446
[12]   Syntheses of optically active α-amino nitriles by asymmetric transformation of the second kind using a principle of O.!Dimroth [J].
Hassan, NA ;
Bayer, E ;
Jochims, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (22) :3747-3757
[13]   BENZYLATION AND RELATED ALKYLATIONS OF ALPHA-DIMETHYLAMINOPHENYLACETONITRILE BY MEANS OF ALKALI AMIDES - DEHYDROCYANATION OF PRODUCTS TO FORM ENAMINES [J].
HAUSER, CR ;
TAYLOR, HM ;
LEDFORD, TG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (07) :1786-1789
[14]  
Hofmann A.W., 1883, Berichte der deutschen chemischen Gesellschaft, V16, P558, DOI DOI 10.1002/CBER.188301601120
[15]   New yttrium complexes bearing diamidoamine ligands as efficient and diastereoselective catalysts for the intramolecular hydroamination of alkenes and alkynes [J].
Hultzsch, KC ;
Hampel, F ;
Wagner, T .
ORGANOMETALLICS, 2004, 23 (11) :2601-2612
[16]   A NOVEL (5E,9Z)-DIALKYLINDOLIZIDINE FROM THE ANT MONOMORIUM-SMITHII [J].
JONES, TH ;
LADDAGO, A ;
DON, AW ;
BLUM, MS .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (02) :375-381
[17]   INFLUENCE OF A HYDROALCOHOLIC SOLVENT ON THE ENANTIOSELECTIVITY OF ALPHA-AMINO NITRILE HYDRATION CATALYZED BY CHIRAL KETONES [J].
LAGRIFFOUL, PH ;
TADROS, Z ;
TAILLADES, J ;
COMMEYRAS, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (08) :1279-1285
[18]   SYNTHESIS OF MYOSMINE AND NORNICOTINE, USING AN ACYL CARBANION EQUIVALENT AS AN INTERMEDIATE [J].
LEETE, E ;
CHEDEKEL, MR ;
BODEM, GB .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (26) :4465-4466
[20]   About a new formation of N-alkalized Pyrrolidine. [J].
Loffler, K ;
Freytag, C .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1909, 42 :3427-3431