Organocatalytic asymmetric hydrophosphination of α,β-Unsaturated aldehydes

被引：151

作者：

Carlone, Armando ^{[1
]}

Bartoli, Giuseppe ^{[1
]}

Bosco, Marcella ^{[1
]}

Sambri, Letizia ^{[1
]}

Melchiorre, Paolo ^{[1
]}

机构：

[1] Univ Bologna, Dept Organ Chem A Mangini Alma Mater Studiorum, I-40136 Bologna, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 24期

关键词：

aldehydes; asymmetric synthesis; conjugate addition; organocatalysis; phosphanes;

D O I：

10.1002/anie.200700754

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Getting round the (periodic) table: A highly chemo- and enantioselective conjugate addition of diphenylphosphine to α,β-unsaturated aldehydes in the presence of a chiral secondary amine C provides a direct route to chiral β-phosphino aldehyde intermediates (see scheme, TMS = trimethylsilyl). The synthetic utility of the strategy was exemplified in a rapid one-pot (two-step) synthesis of highly enantioenriched 3-amino-phosphines. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4504 / 4506

页数：3

共 67 条

[31] A general organocatalyst for direct α-functionalization of aldehydes:: Stereoselective C-C, C-N, C-F, C-BR, and C-S bond-forming reactions.: Scope and mechanistic insights [J].

Franzén, J ;

Marigo, M ;

Fielenbach, D ;

Wabnitz, TC ;

Kjaersgaard, A ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18296-18304

[32] Enantioselective organocatalysis [J].

Gaunt, Matthew J. ;

Johansson, Carin C. C. ;

McNally, Andy ;

Vo, Ngoc T. .

DRUG DISCOVERY TODAY, 2007, 12 (1-2) :8-27

[33] Organocatalytic synthesis of chiral benzopyrans [J].

Govender, Thavendran ;

Hojabri, Leila ;

Moghaddam, Frouz Matloubi ;

Arvidsson, Per I. .

TETRAHEDRON-ASYMMETRY, 2006, 17 (12) :1763-1767

[34] The development of bidentate P,N ligands for asymmetric catalysis [J].

Guiry, PJ ;

Saunders, CP .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (05) :497-537

[35] Direct organocatalytic asymmetric α-chlorination of aldehydes [J].

Halland, N ;

Braunton, A ;

Bachmann, S ;

Marigo, M ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) :4790-4791

[36] Enantioselective organo-cascade catalysis [J].

Huang, Y ;

Walji, AM ;

Larsen, CH ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :15051-15053

[37]

Ibrahem I., 2007, ANGEW CHEM, V119, P4591, DOI DOI 10.1002/ANGE.200700916

[38] Enantioselective organocatalytic hydrophosphination of α,β-unsaturated aldehydes [J].

Ibrahem, Ismail ;

Rios, Ramon ;

Vesely, Jan ;

Hammar, Peter ;

Eriksson, Lars ;

Himo, Fahmi ;

Cordova, Armando .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4507-4510

[39] New strategies for organic catalysis: The first enantioselective organocatalytic 1,3-dipolar cycloaddition [J].

Jen, WS ;

Wiener, JJM ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (40) :9874-9875

[40]

Lelais G, 2006, ALDRICHIM ACTA, V39, P79

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