Efficient addition reaction of bromonitromethane to aldehydes catalyzed by NaI:: A new route to 1-bromo-1-nitroalkan-2-ols under very mild conditions

被引：24
|
作者：
Concellon, Jose M.
Rodriguez-Solla, Humberto
Concellon, Carmen
Garcia-Granada, Santiago
Rosario Diaz, M.
机构：
[1] Univ Oviedo, Dept Quim Organ & Inorgan, Fac Quim, E-33071 Oviedo, Spain
[2] Univ Oviedo, Dept Quim Fis & Analit, Fac Quim, E-33071 Oviedo, Spain
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 26期
关键词：
D O I：
10.1021/ol062451f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic NaI-mediated novel synthesis of 1-bromo-1-nitroalkan-2-ols was carried out by reaction of bromonitromethane with a variety of aldehydes, under very mild conditions. When the reaction was performed with chiral N, N- dibenzyl alaninal, the corresponding enantiopure ( 1 S, 2 S, 3 S)- 3- dibenzylamino- 1- bromo- 1- nitrobutan- 2- ol was obtained with good stereoselectivity. The structure of this enantiopure bromohydrin was established by X- ray analysis.
引用
收藏
页码：5979 / 5982
页数：4
相关论文
共 34 条
  • [11] N-Hydroxyphthalimide-catalyzed radical addition of 1,3-dioxolanes and molecular oxygen to alkenes under ambient conditions:: a new route to β-oxycarbonyl compounds
    Hirano, K
    Iwahama, T
    Sakaguchi, S
    Ishii, Y
    CHEMICAL COMMUNICATIONS, 2000, (24) : 2457 - 2458
  • [12] THE PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF 2-BROMO-ARYLMERCURY COMPOUNDS AND 2-BROMO-ARYL IODIDES WITH ALPHA,BETA-ENONES - A NEW ENTRY TO 1-INDANOLS
    CACCHI, S
    PALMIERI, G
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 282 (01) : C3 - C6
  • [13] New Efficient Synthesis of 1,2,4-Trisubstituted Furans by a Sequential Passerini/Wittig/Isomerization Reaction Starting from Baylis-Hillman β-Bromo Aldehydes
    Ren, Zhi-Lin
    Sun, Mei
    Guan, Zhi-Rong
    Ding, Ming-Wu
    SYNLETT, 2018, 29 (01) : 106 - 110
  • [14] A Mild and Efficient Copper Catalyzed Synthesis of 1,2,3-Triazolo Quinoxalines under Click Conditions (vol 60, pg 1173, 2024)
    Bommera, Ravi Kumar
    Eppakayala, Laxminarayana
    Kethireddy, Shashikala
    Vudari, Balaraju
    Syeda, Asra Banu
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (08) : 1618 - 1618
  • [15] An efficient one-step synthesis of 1,4-dihydropyridines via a triphenylphosphine-catalyzed three-component Hantzsch reaction under mild conditions
    Debache, Abdelmadjid
    Ghalem, Wassima
    Boulcina, Raouf
    Belfaitah, Ali
    Rhouati, Salah
    Carboni, Bertrand
    TETRAHEDRON LETTERS, 2009, 50 (37) : 5248 - 5250
  • [16] Ruthenium-catalyzed Biginelli condensation:: A simple and efficient one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones under mild reaction conditions
    Jain, Suman L.
    Sharma, Vishal B.
    Sain, Bir
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (03) : 777 - 779
  • [17] An unexpected palladium-catalyzed reaction of 2-alkynylhalobenzene with 2-alkynylaniline: a novel and efficient route to 11H-indeno[1,2-c]quinolin-11-ols
    Pan, Xiaolin
    Luo, Yong
    Wu, Jie
    CHEMICAL COMMUNICATIONS, 2011, 47 (31) : 8967 - 8969
  • [18] AN EFFICIENT SYNTHESIS OF [1,2,4] TRIAZOLO-QUINAZOLINONE DERIVATIVES USING TIN (II) CHLORIDE DIHYDRATE UNDER MILD REACTION CONDITIONS
    Shaikh, Kabeer A.
    Chaudhar, Uddhav N.
    HETEROCYCLIC LETTERS, 2020, 10 (03): : 429 - 434
  • [19] An Efficient Copper-Catalyzed One-Pot Synthesis of 1-Aryl-1,2,3-triazoles from Arylboronic Acids in Water under Mild Conditions
    Hao, Changbo
    Zhou, Changjian
    Xie, Jianwei
    Zhang, Jie
    Liu, Ping
    Dai, Bin
    CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (11) : 1317 - 1320
  • [20] New Copper(I) oxide biocatalyst based on functionalized olive stone for the synthesis of 1,4-disubstituted-1,2,3-triazoles under very mild conditions
    Forte-Castro, Arantxa
    Perez, Juana M.
    Garcia-Manas, Celia
    Garcia-Garcia, Gracia
    Urquiza, Pedro
    Romacho, Tania
    Fernandez, Ignacio
    SUSTAINABLE CHEMISTRY AND PHARMACY, 2024, 42
1234