Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results

被引:518
作者
Ballini, R [1 ]
Bosica, G [1 ]
Fiorini, D [1 ]
Palmieri, A [1 ]
Petrini, M [1 ]
机构
[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy
关键词
D O I
10.1021/cr040602r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nitroalkanes are a valuable source of stabilized carbanions because the high electron-withdrawing power of the nitro group provides an outstanding enhancement of the hydrogen acidity at the α-position. This review covers the utilization of nitroalkanes as nucleophiles in conjugate additions with electron-poor alkenes, as well as the new procedures and related applications appearing in the literature after 1990. Focus is on asymmetric additions carried out using optically active alkenes or with the aid of chiral catalysts.
引用
收藏
页码:933 / 971
页数:39
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共 245 条
[91]  
CHASAR DW, 1982, SYNTHESIS-STUTTGART, P841
[92]   Formal total synthesis of camptothecin via ring-closing metathesis strategy [J].
Chavan, SP ;
Pasupathy, K ;
Venkatraman, MS ;
Kale, RR .
TETRAHEDRON LETTERS, 2004, 45 (37) :6879-6882
[93]  
CHEN YJ, 1993, TETRAHEDRON LETT, V34, P2961
[94]   Stereocontrolled tandem radical cyclization: A new and facile route to syntheses of (+/-)-alpha-biotol and (+/-)-beta-biotol [J].
Chen, YJ ;
Chang, WH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2536-2539
[95]   A FACILE SYNTHESIS OF A DELTA-2-CEDRENE SKELETON VIA TANDEM RADICAL CYCLIZATION [J].
CHEN, YJ ;
LIN, WY .
TETRAHEDRON LETTERS, 1992, 33 (13) :1749-1750
[96]   A facile synthesis of 1,7-dicarbonyl compounds via three-component Michael addition reactions [J].
Chetia, A ;
Saikia, CJ ;
Lekhok, KC ;
Boruah, RC .
TETRAHEDRON LETTERS, 2004, 45 (12) :2649-2651
[97]   SYNTHESIS OF NOVEL CYCLIC HYDROXAMIC ACIDS [J].
CHITTARI, P ;
THOMAS, A ;
RAJAPPA, S .
TETRAHEDRON LETTERS, 1994, 35 (22) :3793-3796
[98]   Catalytic C-C bond formation promoted by Mg-Al-O-t-Bu hydrotalcite [J].
Choudary, BM ;
Kantam, ML ;
Kavita, B ;
Reddy, CV ;
Figueras, F .
TETRAHEDRON, 2000, 56 (47) :9357-9364
[99]   Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].
Christoffers, J ;
Baro, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690
[100]   FLUORIDE-ION AS A BASE IN ORGANIC-SYNTHESIS [J].
CLARK, JH .
CHEMICAL REVIEWS, 1980, 80 (05) :429-452