Enantioselective Synthesis of P-Stereogenic Phosphinates and Phosphine oxides by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis

被引：124

作者：

Harvey, James Stephen ^{[2
]}

Malcolmson, Steven J. ^{[1
]}

Dunne, Katherine S. ^{[2
]}

Meek, Simon J. ^{[1
]}

Thompson, Amber L. ^{[2
]}

Schrock, Richard R. ^{[3
]}

Hoveyda, Amir H. ^{[1
]}

Gouverneur, Veronique ^{[2
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

[2] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

[3] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 04期

基金：

美国国家卫生研究院; 英国工程与自然科学研究理事会;

关键词：

enantioselective synthesis; homogeneous catalysis; molybdenum; olefin metathesis; phosphorus; NEUTRAL COORDINATE-ORGANOCATALYSTS; OLEFIN-METATHESIS; CROSS-METATHESIS; SECONDARY PHOSPHINES; ALKYLIDENE COMPLEXES; TERTIARY ETHERS; ALLYLATION; PHOSPHORUS; DESYMMETRIZATION; HETEROCYCLES;

D O I：

10.1002/anie.200805066

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The first catalytic route toward the title compounds by asymmetric ring-closing metathesis is described. A remarkable reversal of enantioselectivity is observed when the achiral imido ligand of the chiral molybdenum-catalyst is changed (see scheme), thus highlighting the importance of the achiral and the chiral ligands in catalyst design. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：762 / 766

页数：5

共 66 条

[21] Catalytic asymmetric deprotonation of phosphine boranes and sulfides as a route to P-stereogenic compounds [J].

Gammon, Jonathan J. ;

Canipa, Steven J. ;

O'Brien, Peter ;

Kelly, Brian ;

Taylor, Sven .

CHEMICAL COMMUNICATIONS, 2008, (32) :3750-3752

[22] Catalytic asymmetric synthesis of ferrocenes and P-stereogenic bisphosphines [J].

Genet, Cedric ;

Canipa, Steven J. ;

O'Brien, Peter ;

Taylor, Sven .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9336-9337

[23] Catalytic asymmetric synthesis of chiral phosphanes [J].

Glueck, David S. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (24) :7108-7117

[24] Ring closing metathesis reactions on a phosphonate template [J].

Hanson, PR ;

Stoianova, DS .

TETRAHEDRON LETTERS, 1998, 39 (23) :3939-3942

[25]

HOVEYDA AH, 2003, HDB METATHESIS, V2, pCH3

[26] The remarkable metal-catalysed olefin metathesis reaction [J].

Hoveyda, Amir H. ;

Zhugralin, Adil R. .

NATURE, 2007, 450 (7167) :243-251

[27] Enantioselective synthesis of cyclic allylboronates by Mo-catalyzed asymmetric ring-closing metathesis (ARCM). A one-pot protocol for net catalytic enantioselective cross metathesis [J].

Jernelius, JA ;

Schrock, RR ;

Hoveyda, AH .

TETRAHEDRON, 2004, 60 (34) :7345-7351

[28] Pallado-catalysed hydrophosphination of alkynes: access to enantio-enriched P-stereogenic vinyl phosphine-boranes [J].

Join, Benoit ;

Mimeau, David ;

Delacroix, Olivier ;

Gaumont, Annie-Claude .

CHEMICAL COMMUNICATIONS, 2006, (30) :3249-3251

[29] Enantioselective synthesis of P-chirogenic phosphorus compounds via the ephedrine-borane complex methodology [J].

Juge, S. .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (2-3) :233-248

[30] EFFICIENT ASYMMETRIC-SYNTHESIS OF OPTICALLY PURE TERTIARY MONO AND DIPHOSPHINE LIGANDS [J].

JUGE, S ;

STEPHAN, M ;

LAFFITTE, JA ;

GENET, JP .

TETRAHEDRON LETTERS, 1990, 31 (44) :6357-6360

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