Enantioselective synthesis of optically active alkanephosphonates via rhodium-catalyzed asymmetric hydrogenation of β-substituted α,β-unsaturated phosphonates with ferrocene-based monophosphoramidite ligands

被引：39

作者：

Duan, Zheng-Chao ^{[1
,2
]}

Hu, Xiang-Ping ^{[1
]}

Wang, Dao-Yong ^{[1
,2
]}

Huang, Jia-Di ^{[1
,2
]}

Yu, Sai-Bo ^{[1
,2
]}

Deng, Jun ^{[1
,2
]}

Zheng, Zhuo ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 13期

基金：

中国国家自然科学基金;

关键词：

alkanephosphonates; asymmetric catalysis; hydrogenation; monophosphoramidite ligands; rhodium;

D O I：

10.1002/adsc.200800388

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A series of chiral beta-substituted alkane-phosphonates was synthesized in high enantioselectivities via the first rhodium-catalyzed asymmetric hydrogenation of the corresponding beta-substituted-alpha,beta-unsaturated phosphonates using a ferrocene-derived rnonophosphoramidite ligand, with which up to 99.5% ee have been achieved for the hydrogenation of (E)-substrates and 98.0% ee for (Z)-substrates.

引用

页码：1979 / 1983

页数：5

共 62 条

[1]

Achiwa K., 1978, Tetrahedron Lett., V19, P1119

[2]

BELLUCCI C, 1989, FARMACO, V44, P1167

[3] The asymmetric synthesis of alpha-substituted alpha-methyl and alpha-phenyl phosphonic acids: Design, carbanion geometry, reactivity and preparative aspects of chiral alkyl bicyclic phosphonamides [J].

Bennani, YL ;

Hanessian, S .

TETRAHEDRON, 1996, 52 (44) :13837-13866

[4] Photo-Arbuzov rearrangements of benzylic phosphites. Stereochemistry at migratory carbon [J].

Bhanthumnavin, W ;

Arif, A ;

Bentrude, WG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7753-7758

[5] Enantioselective synthesis of α-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation [J].

Burk, MJ ;

Stammers, TA ;

Straub, JA .

ORGANIC LETTERS, 1999, 1 (03) :387-390

[6] PHOTOREARRANGEMENTS OF BENZYL PHOSPHITES - STEREOCHEMISTRY AT PHOSPHORUS [J].

CAIRNS, SM ;

BENTRUDE, WG .

TETRAHEDRON LETTERS, 1989, 30 (09) :1025-1028

[7]

Chi YX, 2005, MODERN RHODIUM-CATALYZED ORGANIC REACTIONS, P1, DOI 10.1002/3527604693.ch1

[8] Catalytic homogeneous asymmetric hydrogenations of largely unfunctionalized alkenes [J].

Cui, XH ;

Burgess, K .

CHEMICAL REVIEWS, 2005, 105 (09) :3272-3296

[9] Catalytically distinct antibodies prepared by the reactive immunization versus transition state analogue hapten manifolds [J].

Datta, A ;

Wentworth, P ;

Shaw, JP ;

Simeonov, A ;

Janda, KD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (45) :10461-10467

[10] Enantioselective synthesis of β2-Amino acids via Rh-catalyzed asymmetric hydrogenation with BoPhoz-type ligands:: Important influence of an N-H proton in the ligand on the enantioselectivity [J].

Deng, Jun ;

Hu, Xiang-Ping ;

Huang, Jia-Di ;

Yu, Sai-Bo ;

Wang, Dao-Yong ;

Duan, Zheng-Chao ;

Zheng, Zhuo .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :2015-2017

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