Oxaziridine-mediated enantioselective aminohydroxylation of styrenes catalyzed by copper(II) bis(oxazoline) complexes

被引：71

作者：

Michaelis, David J. ^{[1
]}

Williamson, Kevin S. ^{[1
]}

Yoon, Tehshik P. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

TETRAHEDRON | 2009年 / 65卷 / 26期

关键词：

SHARPLESS ASYMMETRIC AMINOHYDROXYLATION; CHIRAL BIS(OXAZOLINE); AMINOACETOXYLATION; AMINOOXYGENATION; CONSTRUCTION; CYCLIZATION; EFFICIENT; LIGANDS; ALKENES; SCOPE;

D O I：

10.1016/j.tet.2009.03.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an oxaziridine-mediated enantioselective aminohydroxylation of olefins catalyzed by a chiral copper(II) bis(oxazoline) complex. A variety of styrenic olefins undergo efficient aminohydroxylation with excellent regioselectivity and synthetically useful levels of enantioselectivity (up to 84% ee). The reaction can be conducted on multi-gram scale with as little as 2 mol % of the copper(II) catalyst. Hydrolysis of the resulting 1,3-oxazolines under acidic conditions produces N-sulfonyl amino alcohols that can be purified by recrystallization to afford very high levels of enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5118 / 5124

页数：7

相关论文

共 39 条

[1] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].

Alexanian, EJ ;

Lee, C ;

Sorensen, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691

[2] Lewis acid-catalyzed [4+2] benzannulation between enynal units and enols or enol ethers: Novel synthetic tools for polysubstituted aromatic compounds including indole and benzofuran derivatives [J].

Asao, Naoki ;

Aikawa, Haruo .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5249-5253

[3] The synthesis of vicinal amino alcohols [J].

Bergmeier, SC .

TETRAHEDRON, 2000, 56 (17) :2561-2576

[4] The Sharpless asymmetric aminohydroxylation [J].

Bodkin, JA ;

McLeod, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24) :2733-2746

[5] Total synthesis of the vancomycin aglycon [J].

Boger, DL ;

Miyazaki, S ;

Kim, SH ;

Wu, JH ;

Castle, SL ;

Loiseleur, O ;

Jin, Q .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10004-10011

[6] Total synthesis of ustiloxin D [J].

Cao, B ;

Park, H ;

Joullié, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (04) :520-521

[7] Hg(II) reagent-controlled stereoselective synthesis of 2,5-cis- and 2,5-trans-polyhydroxylated pyrrolidines [J].

Chikkanna, D ;

Han, HS .

SYNLETT, 2004, (13) :2311-2314

[8] Metal-Free Oxidative Cyclization of Urea-Tethered Alkenes with Hypervalent Iodine [J].

Cochran, Brian M. ;

Michael, Forrest E. .

ORGANIC LETTERS, 2008, 10 (21) :5039-5042

[9] Mild electrochemical deprotection of N-phenylsulfonyl N-substituted amines derived from (R)-phenylglycinol [J].

Coeffard, Vincent ;

Thobie-Gautier, Christine ;

Beaudet, Isabelle ;

Le Grognec, Erwan ;

Quintard, Jean-Paul .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (02) :383-391

[10] An efficient and general one-pot method for the synthesis of chiral bis(oxazoline) and pyridine bis(oxazoline) ligands [J].

Cornejo, A ;

Fraile, JM ;

García, JI ;

Gil, MJ ;

Martínez-Merino, V ;

Mayoral, JA ;

Pires, E ;

Villalba, I .

SYNLETT, 2005, (15) :2321-2324

← 1 2 3 4 →