The Sharpless asymmetric aminohydroxylation

被引：176

作者：

Bodkin, JA ^{[1
]}

McLeod, MD ^{[1
]}

机构：

[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 24期

关键词：

D O I：

10.1039/b111276g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sharpless asymmetric aminohydroxylation (AA) reaction was discussed. The reaction employed a catalyst consisting of cinchona alkaloid derived ligand and an osmium species in combination with a stoichiometric nitrogen source. The ligand increased the rate of the reaction, influenced regioselectivity and induced enantioselectivity in the AA reactions. The three nitrogen sources used in the reaction were sulfonamides, carbamates and amides.

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收藏

页码：2733 / 2746

页数：14

相关论文

共 118 条

[101] REMOVAL OF N-ARYLSULFONYL GROUPS FROM HYDROXY ALPHA-AMINO-ACIDS [J].

ROEMMELE, RC ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2367-2371

[102] A highly efficient aminohydroxylation process [J].

Rubin, AE ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2637-2640

[103] Smaller substituents on nitrogen facilitate the osmium-catalyzed asymmetric aminohydroxylation [J].

Rudolph, J ;

Sennhenn, PC ;

Vlaar, CP ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2810-2813

[104] OSMIUM-CATALYZED VICINAL OXYAMINATIONS OF OLEFINS BY CHLORAMINE-T [J].

SHARPLESS, KB ;

CHONG, AO ;

OSHIMA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (01) :177-179

[105]

SHARPLESS KB, 1997, Patent No. 19975767304

[106]

SHARPLESS KB, 2002, Patent No. 20026350905

[107] Silica gel supported bis-cinchona alkaloid: A highly efficient chiral ligand for heterogeneous asymmetric dihydroxylation of olefins [J].

Song, CE ;

Yang, JW ;

Ha, HJ .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :841-844

[108] One-step synthesis of paclitaxel side-chain precursor:: benzamide-based asymmetric aminohydroxylation of isopropyl trans-cinnamate [J].

Song, CE ;

Oh, CR ;

Roh, EJ ;

Lee, SG ;

Choi, JH .

TETRAHEDRON-ASYMMETRY, 1999, 10 (04) :671-674

[109] tert-butylsulfonyl (Bus), a new protecting group for amines [J].

Sun, P ;

Weinreb, SM ;

Shang, MY .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8604-8608

[110] Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates [J].

Tao, B ;

Schlingloff, G ;

Sharpless, KB .

TETRAHEDRON LETTERS, 1998, 39 (17) :2507-2510

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