Synthesis and applications of (R)- and (S)-7,7′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene

被引：24

作者：

Che, DQ ^{[1
]}

Andersen, NG ^{[1
]}

Lau, SYW ^{[1
]}

Parvez, M ^{[1
]}

Keay, BA ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 09期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0957-4166(00)00148-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of (R)- and (S)-7,7'-dimethoxy-2,2' -bis(diphenylphosphino)-1,1'-binaphthalene 5a and 5b is described. The phosphorus atoms in (S)-(-)-5b are shown to be slightly more basic than the phosphorus atoms in (S)-BINAP by comparing the magnitude of the (1)J((31)p-Se-77) coupling constant in their respective diselenide derivatives. (S)-(-)-5b behaved similarly to (S)-BINAP in asymmetric Heck reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1919 / 1925

页数：7

相关论文

共 26 条

[1] Convenient and direct preparation of tertiary phosphines via nickel-catalysed cross-coupling [J].

Ager, DJ ;

East, MB ;

Eisenstadt, A ;

Laneman, SA .

CHEMICAL COMMUNICATIONS, 1997, (24) :2359-2360

[2]

*ALDR CHEM COMP, 36 ALDR CHEM COMP, P750

[3] THE CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .15. P-31 NUCLEAR MAGNETIC-RESONANCE STUDIES OF THE DONOR PROPERTIES OF HETEROARYLPHOSPHINES TOWARDS SELENIUM AND PLATINUM(II) [J].

ALLEN, DW ;

TAYLOR, BF .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1982, (01) :51-54

[4] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].

Ashimori, A ;

Bachand, B ;

Overman, LE ;

Poon, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487

[5]

Barthel-Rosa LP, 1999, COORDIN CHEM REV, V190, P587

[6] Preparation and use of a polymer supported BINAP hydrogenation catalyst [J].

Bayston, DJ ;

Fraser, JL ;

Ashton, MR ;

Baxter, AD ;

Polywka, MEC ;

Moses, E .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :3137-3140

[7] SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].

CAI, DW ;

PAYACK, JF ;

BENDER, DR ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181

[8]

CAI DW, 1996, Patent No. 08311090

[9] CHIRAL RECOGNITION IN CLEFTS AND CYCLOPHANE CAVITIES SHAPED BY THE 1,1'-BINAPHTHYL MAJOR GROOVE [J].

CASTRO, PP ;

GEORGIADIS, TM ;

DIEDERICH, F .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5835-5838

[10] Fluorous biphase systems - The new phase-separation and immobilization technique [J].

Cornils, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (19) :2057-2059