Facile synthesis of 2-nitroalkanols by tetramethylguanidine (TMG)-catalyzed addition of primary nitroalkanes to aldehydes and alicyclic ketones

被引：71

作者：

Simoni, D

Invidiata, FP

Manfredini, S

Ferroni, R

Lampronti, I

Roberti, M

Pollini, GP

机构：

[1] UNIV FERRARA,DIPARTIMENTO SCI FARMACEUT,I-44100 FERRARA,ITALY

[2] UNIV BOLOGNA,DIPARTIMENTO SCI FARMACEUT,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(97)00461-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetramethylguanidine-catalyzed addition of primary nitroalkanes to aldehydes and alicyclic ketones constitutes a practical means to perform the nitro-aldol reaction (Henry reaction). The very mild conditions employed, together with the short reaction times, make the procedure tolerant of a range of functionalities and highly versatile for the synthesis of a variety of 2-nitroalkanols. (C) 1997 Elsevier Science Ltd.

引用

页码：2749 / 2752

页数：4

共 15 条

[1] [Anonymous], COMPREHENSIVE ORGANI
[2] [Anonymous], 1971, NITRILE OXIDES
[3] Baer H. H., 1970, CHEM NITRO NITROSO G, V2
[4] Dauben Jr H. J., 1963, ORG SYNTH, V4, P221
[5] Henry L. C. R., 1895, C. R. H. Acad. Sci, V120, P1265
[6] CONJUGATE ADDITION TO THE ETHYLENE KETAL OF 2-CARBOMETHOXY-2-CYCLOPENTENONE - A SYNTHESIS OF SARKOMYCIN
HEWSON, AT
MACPHERSON, DT
[J]. TETRAHEDRON LETTERS, 1983, 24 (06) : 647 - 648
[7] SYNTHESES AND SELECTED REDUCTIONS OF CONJUGATED NITROALKENES - A REVIEW
KABALKA, GW
VARMA, RS
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1987, 19 (4-5) : 283 - 328
[8] ALIPHATIC NITRO-COMPOUNDS .18. INTERACTION OF KETONES AND NITRO-PARAFFINS
LAMBERT, A
LOWE, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1947, (NOV): : 1517 - 1519
[9] SYNTHESIS AND ANTIFUNGAL ACTIVITY OF NEW NITRO-ALCOHOL DERIVATIVES
MIKITE, G
JAKUCS, E
KISTAMAS, A
DARVAS, F
LOPATA, A
[J]. PESTICIDE SCIENCE, 1982, 13 (05): : 557 - 562
[10] POLLINI GP, 1972, SYNTH-INT J METHODS, P44

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