Efficient acyclic stereocontrol using the tethered aminohydroxylation reaction

被引：41

作者：

Donohoe, TJ

Johnson, PD

Pye, RJ

Keenan, M

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Eli Lilly & Co Ltd, Lilly Res Ctr, Windlesham GU20 6PH, Surrey, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 15期

关键词：

D O I：

10.1021/ol049136i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tethered aminohydroxylation (TA) of acyclic allylic carbamates has been achieved in a stereospecific and stereoselective manner. Unusually high levels of stereocontrol were observed in the oxidation of 1,1-disubstituted substrates.

引用

页码：2583 / 2585

页数：3

共 18 条

[1] Regio- and diastereoselective catalytic epoxidation of acyclic allylic alcohols with methyltrioxorhenium:: A mechanistic comparison with metal (peroxy and peroxo complexes) and nonmetal (peracids and dioxirane) oxidants [J].

Adam, W ;

Mitchell, CM ;

Saha-Möller, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3699-3707

[2] Asymmetric amino-hydroxylation of dienylsilanes. An efficient route to amino-cyclitols. [J].

Angelaud, R ;

Landais, Y ;

Schenk, K .

TETRAHEDRON LETTERS, 1997, 38 (08) :1407-1410

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

Bergmeier, SC .

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

[4]

BODKIN JA, 2002, J CHEM SOC P1, V24, P2733

[5] N-bromoacetamide - A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins [J].

Bruncko, M ;

Schlingloff, G ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1483-1486

[6]

CHANG HT, 1996, ANGEW CHEM INT EDIT, V35, P2813

[7] The tethered aminohydroxylation (TA) reaction [J].

Donohoe, TJ ;

Johnson, PD ;

Pye, RJ .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (12) :2025-2028

[8] The tethered aminohydroxylation (TA) of cyclic allylic carbamates [J].

Donohoe, TJ ;

Johnson, PD ;

Cowley, A ;

Keenan, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :12934-12935

[9]

Donohoe TJ, 2001, CHEM COMMUN, P2078

[10] syn stereocontrol in the directed dihydroxylation of acyclic allylic alcohols [J].

Donohoe, TJ ;

Newcombe, NJ ;

Waring, MJ .

TETRAHEDRON LETTERS, 1999, 40 (38) :6881-6885

← 1 2 →