A General Thermolabile Protecting Group Strategy for Organocatalytic Metal-Organic Frameworks

被引：302

作者：

Lun, David J. ^{[1
]}

Waterhouse, Geoffrey I. N. ^{[2
]}

Telfer, Shane G. ^{[1
]}

机构：

[1] Massey Univ, Inst Fundamental Sci, MacDiarmid Inst Adv Mat & Nanotechnol, Palmerston North, New Zealand

[2] Univ Auckland, Dept Chem, Auckland, New Zealand

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 15期

关键词：

HETEROGENEOUS ASYMMETRIC CATALYSIS; PROLINE-DERIVATIVES; ALDOL REACTIONS; DESIGN; AMINE; SIZE; MOFS;

D O I：

10.1021/ja202223d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present a general strategy for incorporating organocatalytic moieties into metal organic frameworks (MOFs). The organocatalytic units are protected by a thermolabile protecting group during MOF synthesis and then unveiled by a simple postsynthetic heating step. The strategy is exemplified using a thermolabile tert-butoxycarbonyl (Boc) protecting group for a proline moiety, the removal of which endows the resulting cubic zinc(II) IRMOF with catalytic activity for asymmetric aldol reactions. The bulky Boc groups also prevent framework interpenetration, producing open MOFs that can admit relatively large substrates.

引用

页码：5806 / 5809

页数：4

共 40 条

[21] Homochiral H-bonded proline based metal organic frameworks [J].

Ingleson, Michael J. ;

Bacsa, John ;

Rosseinsky, Matthew J. .

CHEMICAL COMMUNICATIONS, 2007, (29) :3036-3038

[22] Metal-organic framework materials as catalysts [J].

Lee, JeongYong ;

Farha, Omar K. ;

Roberts, John ;

Scheidt, Karl A. ;

Nguyen, SonBinh T. ;

Hupp, Joseph T. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (05) :1450-1459

[23] Proline-catalyzed direct asymmetric aldol reactions [J].

List, B ;

Lerner, RA ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2395-2396

[24] Engineering Homochiral Metal-Organic Frameworks for Heterogeneous Asymmetric Catalysis and Enantioselective Separation [J].

Liu, Yan ;

Xuan, Weimin ;

Cui, Yong .

ADVANCED MATERIALS, 2010, 22 (37) :4112-4135

[25] Designing Metal-Organic Frameworks for Catalytic Applications [J].

Ma, Liqing ;

Lin, Wenbin .

FUNCTIONAL METAL-ORGANIC FRAMEWORKS: GAS STORAGE, SEPARATION AND CATALYSIS, 2010, 293 :175-205

[26] Enantioselective catalysis with homochiral metal-organic frameworks [J].

Ma, Liqing ;

Abney, Carter ;

Lin, Wenbin .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (05) :1248-1256

[27] The advent and development of organocatalysis [J].

MacMillan, David W. C. .

NATURE, 2008, 455 (7211) :304-308

[28] Organocatalytic direct asymmetric aldol reactions in water [J].

Mase, N ;

Nakai, Y ;

Ohara, N ;

Yoda, H ;

Takabe, K ;

Tanaka, F ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (03) :734-735

[29] Asymmetric enamine catalysis [J].

Mukherjee, Santanu ;

Yang, Jung Woon ;

Hoffmann, Sebastian ;

List, Benjamin .

CHEMICAL REVIEWS, 2007, 107 (12) :5471-5569

[30] Supercritical Processing as a Route to High Internal Surface Areas and Permanent Microporosity in Metal-Organic Framework Materials [J].

Nelson, Andrew P. ;

Farha, Omar K. ;

Mulfort, Karen L. ;

Hupp, Joseph T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :458-+

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