First Iridium-Catalyzed Highly Enantioselective Hydrogenation of β-Nitroacrylates

被引：22

作者：

Li, Shengkun ^{[1
]}

Xiao, Taifeng ^{[1
]}

Li, Dangdang ^{[1
]}

Zhang, Xumu ^{[2
,3
]}

机构：

[1] Nanjing Agr Univ, Coll Plant Protect, Dept Pesticide Sci, Nanjing 210095, Jiangsu, Peoples R China

[2] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

[3] Rutgers State Univ, Dept Pharmaceut Chem, Piscataway, NJ 08854 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 15期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC HYDROGENATION; BETA(2)-AMINO ACIDS; ALPHA-AMINOMETHYLACRYLATES; ACYLAMINO NITROOLEFINS; NITROALKENES; DERIVATIVES; ACRYLATES; PEPTIDES; LIGANDS;

D O I：

10.1021/acs.orglett.5b01758

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first highly chemo- and enantioselective hydrogenation of beta-nitroacrylates was accomplished with an iridium catalyst (Ir-4) with yields and enantioselectivities of up to 96% and 98% ee, respectively. The resulting alpha chiral beta-nitro propionates are attractive building blocks for the synthesis of chiral beta(2)-amino acids, which are the core scaffolds of bioactive natural products, pharmaceuticals, and beta-peptides.

引用

收藏

页码：3782 / 3785

页数：4

相关论文

共 24 条

[11] Synthesis of a new class of conformationally rigid phosphino-oxazolines: Highly enantioselective ligands for Ir-catalyzed asymmetric hydrogenation [J].

Liu, D ;

Tang, WJ ;

Zhang, X .

ORGANIC LETTERS, 2004, 6 (04) :513-516

[12] Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase [J].

Liu, Yan-Jie ;

Pei, Xiao-Qiong ;

Lin, Hui ;

Gai, Ping ;

Liu, Yu-Chang ;

Wu, Zhong-Liu .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2012, 95 (03) :635-645

[13] Organocatalytic asymmetric transferhydrogenation of β-nitroacrylates:: Accessing β2-amino acids [J].

Martin, Nolwenn J. A. ;

Cheng, Xu ;

List, Benjamin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (42) :13862-13863

[14] Nakinadines B-F:: new pyridine alkaloids with a β-amino acid moiety from sponge Amphimedon sp. [J].

Nishi, Takami ;

Kubota, Takaaki ;

Fromont, Jane ;

Sasaki, Takuma ;

Kobayashi, Jun'ichi .

TETRAHEDRON, 2008, 64 (14) :3127-3132

[15] STEREOSELECTIVE HYDROGENATION VIA DYNAMIC KINETIC RESOLUTION [J].

NOYORI, R ;

IKEDA, T ;

OHKUMA, T ;

WIDHALM, M ;

KITAMURA, M ;

TAKAYA, H ;

AKUTAGAWA, S ;

SAYO, N ;

SAITO, T ;

TAKETOMI, T ;

KUMOBAYASHI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) :9134-9135

[16]

Ono N., 2001, NITRO GROUP ORGANIC

[17] Enantioselective hydrogenation of α-aminomethylacrylates containing a free N-H group for the synthesis of β-amino acid derivatives [J].

Qiu, Liqin ;

Prashad, Mahavir ;

Hu, Bin ;

Prasad, Kapa ;

Repic, Oljan ;

Blacklock, Thomas J. ;

Kwong, Fuk Yee ;

Kok, Stanton H. L. ;

Lee, Hang Wai ;

Chan, Albert S. C. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16787-16792

[18] Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins [J].

Schneider, Jakob F. ;

Lauber, Markus B. ;

Muhr, Vanessa ;

Kratzer, Domenic ;

Paradies, Jan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (11) :4323-4327

[19] Transfer Hydrogenation in Water: Enantioselective, Catalytic Reduction of (E)-β,β-Disubstituted Nitroalkenes [J].

Soltani, Omid ;

Ariger, Martin A. ;

Carreira, Erick M. .

ORGANIC LETTERS, 2009, 11 (18) :4196-4198

[20] Asymmetric bioreductions of β-nitro acrylates as a route to chiral β2-Amino acids [J].

Swiderska, Magdalena A. ;

Stewart, Jon D. .

ORGANIC LETTERS, 2006, 8 (26) :6131-6133