Platinum-catalyzed asymmetric alkylation of secondary phosphines: Enantioselective synthesis of P-stereogenic phosphines

被引：179

作者：

Scriban, C ^{[1
]}

Glueck, DS ^{[1
]}

机构：

[1] Dartmouth Coll, Dept Chem, Burke Lab 6128, Hanover, NH 03755 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 09期

关键词：

D O I：

10.1021/ja058096q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The chiral Pt catalyst precursor Pt((R,R)-Me-Duphos)(Ph)(Cl) mediated alkylation of racemic secondary phosphines PHR(R′) with benzyl halides in the presence of base to give enantioenriched tertiary phosphines PR(R′)(CH2Ar). Similar reactions of bis(secondary) phosphines yielded chiral diphosphines in up to 93% ee and with good rac/meso diastereoselection. Copyright © 2006 American Chemical Society.

引用

页码：2788 / 2789

页数：2

共 26 条

[1]

Blaser H.U., 2004, ASYMMETRIC CATALYSIS

[2] Chiral palladium(0) trans-stilbene complexes:: Synthesis, structure, and oxidative addition of phenyl iodide [J].

Brunker, TJ ;

Blank, NF ;

Moncarz, JR ;

Scriban, C ;

Anderson, BJ ;

Glueck, DS ;

Zakharov, LN ;

Golen, JA ;

Sommer, RD ;

Incarvito, CD ;

Rheingold, AL .

ORGANOMETALLICS, 2005, 24 (11) :2730-2746

[3] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ ;

FEASTER, JE ;

NUGENT, WA ;

HARLOW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138

[4] New P-chirogenic phosphine ligands and their use in catalytic asymmetric reactions [J].

Crépy, KVL ;

Imamoto, T .

NEW ASPECTS IN PHOSPHORUS CHEMISTRY III, 2003, 229 :1-40

[5] STEREOSELECTIVE SYNTHESES OF COORDINATED SECONDARY AND TERTIARY PHOSPHINES - CRYSTAL AND MOLECULAR-STRUCTURE OF [(R-STAR,R-STAR),(R-STAR)]-(+/-(-[(ETA-5-C5H5)(1,2-C6H4(PMEPH)2)FE-(PHMEPH)]PF6.0.5CH2CL2 [J].

CRISP, GT ;

SALEM, G ;

WILD, SB ;

STEPHENS, FS .

ORGANOMETALLICS, 1989, 8 (10) :2360-2367

[6] A SIMPLE METHOD FOR ENRICHING THE ENANTIOMERIC PURITY OF A FUNCTIONAL MOLECULE ALREADY RICH IN ONE ENANTIOMER [J].

FLEMING, I ;

GHOSH, SK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :99-100

[7] Synthesis of both enantiomers of a P-chirogenic 1,2-bisphospholanoethane ligand via convergent routes and application to rhodium-catalyzed asymmetric hydrogenation of CI-1008 (pregabalin) [J].

Hoge, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10219-10227

[8] Recent advances in the synthesis of P(III)-chirogenic compounds [J].

Johansson, MJ ;

Kann, NC .

MINI-REVIEWS IN ORGANIC CHEMISTRY, 2004, 1 (03) :233-247

[9]

Kagan H.B., 1990, CHEM ORGANOPHOSPHORU, V1, P51

[10]

Knowles WS, 2002, ANGEW CHEM INT EDIT, V41, P1999

← 1 2 3 →