Enantioselective Synthesis of Optically Active 3,3-Diarylpropanoates by Conjugate Hydrosilylation with Chiral Rh-bis(oxazolinyl)phenyl Catalysts

被引：25

作者：

Itoh, Kengou ^{[1
]}

Tsuruta, Ayae ^{[1
]}

Ito, Jun-ichi ^{[1
]}

Yamamoto, Yoshihiko ^{[1
]}

Nishiyama, Hisao ^{[1
]}

机构：

[1] Nagoya Univ, Dept Appl Chem, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 23期

基金：

日本学术振兴会;

关键词：

ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; ASYMMETRIC HYDROGENATION; ARYLBORONIC ACIDS; REDUCTION; ESTERS; SUBSTITUENTS; NITROALKENES; COMPLEXES; SULFONES; RECEPTOR;

D O I：

10.1021/jo302357b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate hydrosilylation of 3,3-diarylacrylate derivatives catalyzed by chiral rhodium-bis(oxazolinyl)phenyl complexes (1 mol %) at 60 degrees C for 2 h was investigated to prepare optically active 3,3-diarylpropanoate derivatives in high yields up to 99% yield and high enantioselectivities up to 99%.

引用

页码：10914 / 10919

页数：6

共 31 条

[1] Chiral Bis(oxazolinyl)phenyl RuII Catalysts for Highly Enantioselective Cyclopropanation
Ito, Jun-ichi
Ujiie, Satoshi
Nishiyama, Hisao
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (17) : 4986 - 4990
[2] Optically Active Bis(oxazolinyl)phenyl Metal Complexes as Multipotent Catalysts
Ito, Jun-ichi
Nishiyama, Hisao
ORGANOMETALLIC PINCER CHEMISTRY, 2013, 40 : 243 - +
[3] Enantioselective Hydrosilylation of Aromatic Alkenes Catalyzed by Chiral Bis(oxazolinyl)phenyl-Rhodium Acetate Complexes
Naito, Tatsuo
Yoneda, Takuma
Ito, Jun-ichi
Nishiyama, Hisao
SYNLETT, 2012, (20) : 2957 - 2960
[4] Asymmetric β-boration of α,β-unsaturated carbonyl compounds with chiral Rh[bis(oxazolinyl)phenyl] catalysts
Toribatake, Kenji
Zhou, Li
Tsuruta, Ayae
Nishiyama, Hisao
TETRAHEDRON, 2013, 69 (17) : 3551 - 3560
[5] HIGHLY ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH CHIRAL AND C2-SYMMETRICAL BIS(OXAZOLINYL)PYRIDINE-RHODIUM CATALYSTS
NISHIYAMA, H
KONDO, M
NAKAMURA, T
ITOH, K
ORGANOMETALLICS, 1991, 10 (02) : 500 - 508
[6] Asymmetric synthesis of optically active 3-amino-1,2-diols from N-acyl-protected allylamines via catalytic diboration with Rh[bis(oxazolinyl)phenyl] catalysts
Toribatake, Kenji
Miyata, Suguru
Naganawa, Yuki
Nishiyama, Hisao
TETRAHEDRON, 2015, 71 (21) : 3203 - 3208
[7] Efficient Enantioselective Synthesis of Optically Active Diols by Asymmetric Hydrogenation with Modular Chiral Metal Catalysts
Kadyrov, Renat
Koenigs, Rene M.
Brinkmann, Claus
Voigtlaender, David
Rueping, Magnus
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (41) : 7556 - 7559
[8] ASYMMETRIC CATALYZES .23. OPTICALLY-ACTIVE AMINOPHOSPHANES - SYNTHESIS AND USE IN THE RH-CATALYZED ENANTIOSELECTIVE HYDROSILYLATION
BRUNNER, H
WEBER, H
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (08): : 3380 - 3395
[9] OPTICALLY-ACTIVE PHENANTHROLINES IN ASYMMETRIC CATALYSIS .4. ENANTIOSELECTIVE HYDROSILYLATION OF ACETOPHENONE BY RHODIUM CHIRAL ALKYL PHENANTHROLINE CATALYSTS
GLADIALI, S
PINNA, L
DELOGU, G
GRAF, E
BRUNNER, H
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 937 - 942
[10] Catalytic enantioselective synthesis of quaternary 3,3′-indolyloxindoles by combination of Rh(II) complexes and chiral phosphines
Chen, Dian-Feng
Zhang, Chen-long
Hu, Yue
Han, Zhi-Yong
Gong, Liu-Zhu
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (08): : 956 - 960

← 1 2 3 4 →