Enantioselective Synthesis of Chiral 3-Aryl-1-indanones through Rhodium-Catalyzed Asymmetric Intramolecular 1,4-Addition

被引：44

作者：

Yu, Yue-Na ^{[1
]}

Xu, Ming-Hua ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

基金：

中国国家自然科学基金;

关键词：

CONJUGATE ALKYNYLATION; ARYLBORONIC ACIDS; LIGANDS; INDANONES;

D O I：

10.1021/jo302656s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective synthesis of potentially useful chiral 3-aryl-1-indanones was achieved through a rhodium-catalyzed asymmetric intramolecular 1,4-addition of pinacolborane chalcone derivatives using extraordinary simple Mono-Phos as chiral ligand under relatively mild conditions. This novel protocol offers an easy access to a wide variety of enantioenriched 3-aryl-1-indanone derivatives in high yields (up to 95%) with excellent enantioselectivities (up to 95% ee).

引用

页码：2736 / 2741

页数：6

共 36 条

[21] Stereoselective Palladium-Catalyzed α-Arylation of 3-Aryl-1-Indanones: An Asymmetric Synthesis of (+)-Pauciflorol F [J].

Lee, Bong Hyang ;

Choi, Young Lok ;

Shin, Seunghoon ;

Heo, Jung-Nyoung .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16) :6611-6618

[22] Cationic palladium complex catalyzed highly enantioselective intramolecular addition of arylboronic acids to ketones. A convenient synthesis of optically active cycloalkanols [J].

Liu, Guixia ;

Lu, Xiyan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :16504-16505

[23] Enantioselective Rh(I)-Catalyzed Cyclization of Arylboron Compounds onto Ketones [J].

Low, Darryl W. ;

Pattison, Graham ;

Wieczysty, Martin D. ;

Churchill, Gwydion H. ;

Lam, Hon Wai .

ORGANIC LETTERS, 2012, 14 (10) :2548-2551

[24] 5-PHENYL-3-UREIDOBENZAZEPIN-2-ONES AS CHOLECYSTOKININ-B RECEPTOR ANTAGONISTS [J].

LOWE, JA ;

HAGEMAN, DL ;

DROZDA, SE ;

MCLEAN, S ;

BRYCE, DK ;

CRAWFORD, RT ;

ZORN, S ;

MORRONE, J ;

BORDNER, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (22) :3789-3811

[25] Enantioselective C-C bond cleavage creating chiral quaternary carbon centers [J].

Matsuda, Takanori ;

Shigeno, Masanori ;

Makino, Masaomi ;

Murakami, Masahiro .

ORGANIC LETTERS, 2006, 8 (15) :3379-3381

[26] Synthesis of chiral 3-substituted indanones via an enantioselective reductive-heck reaction [J].

Minatti, Ana ;

Zheng, Xiaolai ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9253-9258

[27]

Natori Y, 2006, HETEROCYCLES, V70, P635

[28] Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones [J].

Nishimura, Takahiro ;

Guo, Xun-Xiang ;

Uchiyama, Nanase ;

Katoh, Taisuke ;

Hayashi, Tamio .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) :1576-+

[29] Rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols: Synthetic equivalent to asymmetric conjugate alkynylation of enones [J].

Nishimura, Takahiro ;

Katoh, Taisuke ;

Takatsu, Keishi ;

Shintani, Ryo ;

Hayashi, Tamio .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14158-+

[30]

PORAS H, 1993, CHEM IND-LONDON, P206

← 1 2 3 4 →