Aldehyde Selective Wacker Oxidations of Phthalimide Protected Allylic Amines: A New Catalytic Route to β3-Amino Acids

被引：123

作者：

Weiner, Barbara ^{[1
]}

Baeza, Alejandro ^{[1
]}

Jerphagnon, Thomas ^{[1
]}

Feringa, Ben L. ^{[1
]}

机构：

[1] Univ Groningen, Dept Organ & Mol Inorgan Chem, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 27期

关键词：

MOLECULAR-OXYGEN; VINYL GROUP; COMPLEXES; REGIOCHEMISTRY; PALLADIUM(II); CYCLIZATION; LIGANDS; OLEFINS;

D O I：

10.1021/ja902591g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new method for the synthesis of B-3-amino acids is presented. Phthalimide protected allylic amines are oxidized under Wacker conditions selectively to aldehydes using PdCl2 and CuCl or Pd(MeCN)(2)Cl(NO2) and CuCl2 as complementary catalyst systems. The aldehydes are produced in excellent yields and exhibit a large substrate scope. B-Amino acids and alcohols are synthesized by oxidation or reduction and subsequent deprotection.

引用

页码：9473 / +

页数：3

共 26 条

[1] CARBOHYDRATES TO CARBOCYCLES - SYNTHESIS OF THE DENSELY FUNCTIONALIZED CARBOCYCLIC CORE OF TETRODOTOXIN BY RADICAL CYCLIZATION OF AN ANHYDRO SUGAR PRECURSOR [J].

ALONSO, RA ;

BURGEY, CS ;

RAO, BV ;

VITE, GD ;

VOLLERTHUN, R ;

ZOTTOLA, MA ;

FRASERREID, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6666-6672

[2] THE TRANSITION-METAL NITRO-NITROSYL REDOX COUPLE - CATALYTIC-OXIDATION OF OLEFINS TO KETONES [J].

ANDREWS, MA ;

KELLY, KP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (10) :2894-2896

[3] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[4] Synthesis of a spirocyclic amine related to the marine natural products halichlorine and pinnaic acid [J].

Clive, DLJ ;

Wang, H ;

Yu, ML .

TETRAHEDRON LETTERS, 2005, 46 (16) :2853-2855

[5] Recent progress in Wacker oxidations: Moving toward molecular oxygen as the sole oxidant [J].

Cornell, Candace N. ;

Sigman, Matthew S. .

INORGANIC CHEMISTRY, 2007, 46 (06) :1903-1909

[6] cis-Dihydroxylation and epoxidation of alkenes by [Mn2O(RCO2)2(tmtacn)2]:: Tailoring the selectivity of a highly H2O2-efficient catalyst [J].

de Boer, JW ;

Brinksma, J ;

Browne, WR ;

Meetsma, A ;

Alsters, PL ;

Hage, R ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :7990-7991

[7] Aminomethyl and aminoacetyl complexes of palladium(II), platinum(II), iron(II) and rhenium(I) with N-phthaloyl as amino protecting group and mechanistic studies on the palladium-catalyzed amidocarbonylation [J].

Enzmann, A ;

Eckert, M ;

Ponikwar, W ;

Polborn, K ;

Schneiderbauer, S ;

Beller, M ;

Beck, W .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2004, (06) :1330-1340

[8] Mono- and binuclear cyclometallated palladium(II) complexes containing bridging (N,O-) and terminal (N-) imidate ligands:: Air stable, thermally robust and recyclable catalysts for cross-coupling processes [J].

Fairlamb, IJS ;

Kapdi, AR ;

Lee, AF ;

Sánchez, G ;

López, G ;

Serrano, JL ;

García, L ;

Pérez, J ;

Pérez, E .

DALTON TRANSACTIONS, 2004, (23) :3970-3981

[9] CATALYTIC-OXIDATION OF ALK-1-ENES TO ALDEHYDES [J].

FERINGA, BL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (12) :909-910

[10] Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].

Feringa, BL .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353

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