Pd-Catalyzed Directed ortho-C-H Alkenylation of Phenylalanine Derivatives

被引：38

作者：

Garcia-Rubia, Alfonso ^{[1
]}

Laga, Eduardo ^{[1
,2
]}

Cativiela, Carlos ^{[2
]}

Urriolabeitia, Esteban P. ^{[2
]}

Gomez-Arrayas, Ramon ^{[1
]}

Carretero, Juan C. ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

[2] Univ Zaragoza, CSIC, Inst Sintesis Quim & Catalisis Homogenea ISQCH, E-50009 Zaragoza, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 06期

关键词：

LATE-STAGE DIVERSIFICATION; BOND FUNCTIONALIZATION; C(SP(3))-H BONDS; AMINO-ACIDS; PD(II)-CATALYZED AMINATION; REMOTE FUNCTIONALIZATION; METHYL-ESTER; N-ACYL; PALLADIUM; OLEFINATION;

D O I：

10.1021/jo502912m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical Pd-catalyzed ortho-olefination of enantioenriched N-(SO2Py)-protected aryl-alanine and norephedrine derivatives with electron-deficient alkenes has been developed using N-fluoro-2,4,6-trimethylpyridinium triflate as the terminal oxidant. The reaction occurs efficiently with excellent monosubstitution selectivity and without loss of enantiopurity. This cross-coupling proved to be broad in scope, tolerating a variety of steric and electronic changes to both coupling partners. Removal of the directing group under mild conditions provides access to optically active tetrahydroisoquinoline-3-carboxylic acid derivatives (Tics) with good diastereocontrol and with very small erosion of enantiomeric purity.

引用

页码：3321 / 3331

页数：11

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