Palladium-Catalyzed Synthesis of Enantiomerically Pure α-Substituted Allylboronic Esters and Their Addition to Aldehydes

被引：25

作者：

Fernandez, Enrique ^{[1
]}

Pietruszka, Joerg ^{[1
]}

Frey, Wolfgang ^{[2
]}

机构：

[1] Univ Dusseldorf, Forschungszentrum Julich, Inst Bioorgan Chem, D-52426 Julich, Germany

[2] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 16期

关键词：

DOUBLE-ALLYLBORATION REACTION; DIELS-ALDER REACTIONS; HIGH OPTICAL PURITY; CARBONYL-ALLYLATION; ASYMMETRIC ALLYLBORATION; STEREOSELECTIVE-SYNTHESIS; ALLYLIC ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; CHIRAL SYNTHESIS; HOMOALLYLIC ALCOHOLS;

D O I：

10.1021/jo1008959

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl(2) to obtain enantiomerically pure alpha-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.

引用

页码：5580 / 5589

页数：10

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