Selective formation of a C3-symmetric P-stereogenic tris(phosphine) via platinum-catalyzed asymmetric alkylation of a tris(secondary phosphine)

被引：7

作者：

Xu, Zhiming ^{[1
]}

Cain, Matthew F. ^{[1
]}

Rupert, Alexander V. ^{[1
]}

Glueck, David S. ^{[1
]}

Golen, James A. ^{[2
]}

Rheingold, Arnold L. ^{[2
]}

机构：

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

[2] Univ Calif San Diego, Dept Chem, La Jolla, CA 92093 USA

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 24期

基金：

美国国家科学基金会;

关键词：

DIASTEREOSELECTIVE CONTROL; METAL-COMPLEXES; LIGANDS; HYDROGENATION; NANOPARTICLES; SPECTROSCOPY; CHEMISTRY; SUBSTRATE; CHIRALITY; SYMMETRY;

D O I：

10.1016/j.tetasy.2015.11.002

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Alkylation of MeC(CH2PHPh)(3) 1 with 2-cyanobenzyl bromide and NaOSiMe3 using the catalyst precursor Pt((R,R)-Me-DuPhos)(Ph)(Cl) gave a mixture of tris(phosphines) enriched in C-3-MeC(CH2PPh(CH2 (o-C-6-H4CN))(3) 3; Cu-catalyzed phosphination yielded C-1-enriched 3. Oxidation of 3 by sulfur or H2O2 formed MeC(CH2P(E)Ph(CH2(o-C6H4CN))(3) (E = S 4; E = O 5). Repeated recrystallization gave a low yield of (R,R,R)-4, which was crystallographically characterized. Tris(phosphine) 3 was formed with a diastereomeric ratio (dr = C-3/C-1) of 2.1(2) and enantiomeric ratios of 54(10) and 3.8(7) for C-3-3 and C-1-3 respectively, which showed that the selectivity of the triple alkylation was not the same at each site (substrate control). (c) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1459 / 1468

页数：10

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