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

[1] Catalytic enantioselective ring-closing metathesis by a chiral biphen-Mo complex [J].

Alexander, JB ;

La, DS ;

Cefalo, DR ;

Hoveyda, AH ;

Schrock, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4041-4042

[2] Substrate and catalyst screening in platinum-catalyzed asymmetric alkylation of bis(secondary) phosphines.: Synthesis of an enantiomerically pure C2-symmetric diphosphine [J].

Anderson, Brian J. ;

Glueck, David S. ;

DiPasquale, Antonio G. ;

Rheingold, Arnold L. .

ORGANOMETALLICS, 2008, 27 (19) :4992-5001

[3]

[Anonymous], ANGEW CHEM

[4] Desymmetrization by direct cross-metathesis producing hitherto unreachable P-stereogenic phosphine oxides [J].

Bisaro, F ;

Gouverneur, V .

TETRAHEDRON, 2005, 61 (09) :2395-2400

[5] Palladium-catalyzed asymmetric phosphination. Scope, mechanism, and origin of enantioselectivity [J].

Blank, Natalia F. ;

Moncarz, Jillian R. ;

Brunker, Tim J. ;

Scriban, Corina ;

Anderson, Brian J. ;

Amir, Omar ;

Glueck, David S. ;

Zakharov, Lev N. ;

Golen, James A. ;

Incarvito, Christopher D. ;

Rheingold, Arnold L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6847-6858

[6] Chirality breeding via asymmetric phosphination. Palladium-catalyzed diastereoselective synthesis of a P-stereogenic phosphine [J].

Blank, NF ;

McBroom, KC ;

Glueck, DS ;

Kassel, WS ;

Rheingold, AL .

ORGANOMETALLICS, 2006, 25 (07) :1742-1748

[7] Ruthenium-catalyzed cross-metathesis between diallylsilanes and electron-deficient Olefins [J].

BouzBouz, Samir ;

Boulard, Lucie ;

Cossy, Janine .

ORGANIC LETTERS, 2007, 9 (19) :3765-3768

[8] THE NUCLEOPHILIC DISPLACEMENT ROUTE TO HOMOCHIRAL ARYLPHOSPHINE OXIDES [J].

BROWN, JM ;

CAREY, JV ;

RUSSELL, MJH .

TETRAHEDRON, 1990, 46 (13-14) :4877-4886

[9] Enantioselective synthesis of P-stereogenic benzophospholanes via palladium-catalyzed intramolecular cyclization [J].

Brunker, Tim J. ;

Anderson, Brian J. ;

Blank, Natalia F. ;

Glueck, David S. ;

Rheingold, Arnold L. .

ORGANIC LETTERS, 2007, 9 (06) :1109-1112

[10] PREPARATION OF ENANTIOMERICALLY PURE PHOSPHINE OXIDES BY NUCLEOPHILIC DISPLACEMENT CHEMISTRY USING OXAZAPHOSPHOLIDINES [J].

CAREY, JV ;

BARKER, MD ;

BROWN, JM ;

RUSSELL, MJH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (07) :831-839

← 1 2 3 4 5 6 7 →