Rhodium-Catalyzed Ring-Opening Reactions of a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene with Arylboronic Acids

被引：29

作者：

Machin, Ben P. ^{[1
]}

Ballantine, Melissa ^{[1
]}

Mandel, Jeremie ^{[2
]}

Blanchard, Nicolas ^{[2
]}

Tam, William ^{[1
]}

机构：

[1] Univ Guelph, Dept Chem, Guelph Waterloo Ctr Grad Work Chem & Biochem, Guelph, ON N1G 2W1, Canada

[2] Univ Haute Alsace, CNRS, Lab Chim Organ & Bioorgan, ENSCMu,FRE 3253, F-68093 Mulhouse, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 19期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ACYL-NITROSO-COMPOUNDS; MESO-BICYCLIC HYDRAZINES; OXABICYCLIC ALKENES; STEREOSELECTIVE CYCLOADDITIONS; ENANTIOSELECTIVE SYNTHESIS; GRIGNARD-REAGENTS; CYCLOADDUCTS; ROUTE; AZABENZONORBORNADIENES; PALLADIUM;

D O I：

10.1021/jo901248w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium-catalyzed ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with arylboronic acids were investigated. The use of [RhCl(COD)](2), (+/-)-BINAP, and NaHCO3 in McOH at 60 degrees C was found to be the optimized conditions for the ring-opening reactions to give the 1,2-ring-opened products. Various arylboronic acids were examined, and low to moderate yields were obtained and stereoselectivities (trans/cis) from 50:50 to 100:0 were observed.

引用

页码：7261 / 7266

页数：6

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