A Study of the Influence of Base, Temperature and Reaction Time in Nitroaldol Reactions Using (R)-(+)-Glyceraldehyde Acetonide: Diastereoselective Synthesis of (4R, 5R)-Dihydro-5-((R)-1,2-Dihydroxyethyl)-4-Nitrofuran-2(3H)-one

被引：6

作者：

Pennaforte, Erica V. ^{[1
]}

Costa, Jeronimo S. ^{[2
]}

Silva, Cristiane A. ^{[1
]}

Saraiva, Marcelo C. ^{[3
]}

Pereira, Vera L. P. ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Lab Sintese Estereosselet Subst Bioativas, Nucleo Pesquisas Prod Nat, BR-21941902 Rio De Janeiro, Brazil

[2] Ctr Fed Educ Tecnol Quim, BR-26530060 Nilopolis, RJ, Brazil

[3] Wyeth Ayerst Res, Chem Dev Pilot Plant, Rouses Point, NY 12979 USA

来源：

LETTERS IN ORGANIC CHEMISTRY | 2009年 / 6卷 / 02期

关键词：

Henry reaction; nitronate ions; nitroalkanes; tetrabutylammonium fluoride; gamma-lactones; HENRY REACTION; EXPEDITIOUS SYNTHESIS; MICHAEL ADDITION; AMINO; ROUTE; NITROMETHANE; ACID; IMINOPOLYOLS; DERIVATIVES; COMPLEXES;

D O I：

10.2174/157017809787582771

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Henry reaction between the nitroalkanes 6-11 and ( R)-(+)- glyceraldehyde acetonide ( 1), was investigated in respect to the variation of the base, temperature and reaction time. Nitroalcohols 5a-f were obtained in good yields (70-85%) and moderate to good anti-selectivities (50-79%). The transformation of the nitroalcohol 5a, b in title gamma-lactone 2, a potential precursor of bioactive beta-aminoacids, was also investigated.

引用

页码：110 / 114

页数：5

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