Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis

被引：428

作者：

Shih, Hui-Wen ^{[1
]}

Vander Wal, Mark N. ^{[1
]}

Grange, Rebecca L. ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 39期

关键词：

VISIBLE-LIGHT PHOTOCATALYSIS; CARBOXYLIC-ACID DERIVATIVES; PHASE-TRANSFER CATALYSIS; C-H FUNCTIONALIZATION; ASYMMETRIC ALKYLATION; RADICALS; PHOTOCHEMISTRY; CYCLOADDITIONS; PHOTOPHYSICS; REDUCTION;

D O I：

10.1021/ja106593m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective aldehyde alpha-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity. The utility of this methodology has been demonstrated via rapid access to an enantioenriched drug target for angiogenesis suppression.

引用

页码：13600 / 13603

页数：4

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