Chiral N,N′-dioxide-Yb(III) complexes catalyzed enantioselective hydrophosphonylation of aldehydes

被引：40

作者：

Chen, Weiliang ^{[1
]}

Hui, Yonghai ^{[1
]}

Zhou, Xin ^{[1
]}

Jiang, Jun ^{[1
]}

Cai, Yunfei ^{[1
]}

Liu, Xiaohua ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 32期

基金：

中国国家自然科学基金;

关键词：

Asymmetric hydrophosphonylation; Aldehydes; N; '-dioxides; Ytterbium; Hydroxy phosphonates; FRIEDEL-CRAFTS ALKYLATION; LI-BINOL COMPLEX; ASYMMETRIC HYDROPHOSPHONYLATION; AL(SALALEN) COMPLEX; TITANIUM ALKOXIDES; BOND FORMATION; PHOSPHONATES; ALDIMINES; SUBSTITUENTS; INHIBITORS;

D O I：

10.1016/j.tetlet.2010.05.137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral N,N'-dioxide-Ytterbium(III) complexes promoted the asymmetric addition of diethyl phosphate to aldehydes, giving the corresponding products with good yields and enantioselectivities. The addition of pyridine favored both reactivity and enantioselectivity. A possible catalytic cycle was proposed to explain the mechanism of the asymmetric hydrophosphonylation of aldehydes. (C) 2010 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4175 / 4178

页数：4

相关论文

共 37 条

[11]

Moore Michael L., 1993, Perspectives in Drug Discovery and Design, V1, P85, DOI 10.1007/BF02171657

[12] Catalytic Enantioselective Hydrophosphonylation of Ketimines Using Cinchona Alkaloids [J].

Nakamura, Shuichi ;

Hayashi, Masashi ;

Hiramatsu, Yuichi ;

Shibata, Norio ;

Funahashi, Yasuhiro ;

Toru, Takeshi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (51) :18240-+

[13] Stereocontrol in asymmetric phospho-aldol catalysis. Chirality relaying in action [J].

Nixon, TD ;

Dalgarno, S ;

Ward, CV ;

Jiang, ML ;

Halcrow, MA ;

Kilner, C ;

Thornton-Pett, M ;

Kee, TP .

COMPTES RENDUS CHIMIE, 2004, 7 (8-9) :809-821

[14] Synthesis of 3,3′-, 6,6′- and 3,3′,6,6′-substituted binaphthols and their application in the asymmetric hydrophosphonylation of aldehydes -: an obvious effect of substituents of BINOL on the enantioselectivity [J].

Qian, CT ;

Huang, TS ;

Zhu, CJ ;

Sun, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (13) :2097-2103

[15] THE ENANTIOSELECTIVE ADDITION OF DIALKYLPHOSPHITES TO ALDEHYDES - CATALYSIS BY A LANTHANUM BINAPHTHOXIDE COMPLEX [J].

RATH, NP ;

SPILLING, CD .

TETRAHEDRON LETTERS, 1994, 35 (02) :227-230

[16] The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: titanium alkoxide-catalyzed P-C bond formation and kinetic resolution [J].

Rowe, BJ ;

Spilling, CD .

TETRAHEDRON-ASYMMETRY, 2001, 12 (12) :1701-1708

[17] Synthesis of an optically active C1-symmetric Al(salalen) complex and its application to the catalytic hydrophosphonylation of aldehydes [J].

Saito, B ;

Katsuki, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) :4600-4602

[18] Synthesis of an optically active Al(salalen) complex and its application to catalytic hydrophosphonylation of aldehydes and aldimines [J].

Saito, Bunnai ;

Egami, Hiromichi ;

Katsuki, Tsutomu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :1978-1986

[19] Enantioselective synthesis of alpha-hydroxy phosphonates using the LaLi(3)tris(binaphthoxide) catalyst (LLB), prepared by an improved method [J].

Sasai, H ;

Bougauchi, M ;

Arai, T ;

Shibasaki, M .

TETRAHEDRON LETTERS, 1997, 38 (15) :2717-2720

[20]

SCHEMMINGER I, 2000, J ORG CHEM, V65, P4818

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