Asymmetric dihydroxylation of allenes

被引：25

作者：

Fleming, SA

Carroll, SM

Hirschi, J

Liu, RM

Pace, JL

Redd, JT

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

[2] So Utah Univ, Dept Chem & Biochem, Cedar City, UT 84720 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 17期

关键词：

alpha-hydroxy ketones;

D O I：

10.1016/j.tetlet.2004.03.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have used asymmetric dihydroxylation (AD) of allenes in order to synthesize chiral of-hydroxy ketones. This methodology has been applied to several aryl-substituted allenes. We have found that electron donating groups on the aromatic ring increase the efficiency of the reaction. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3341 / 3343

页数：3

共 37 条

[31] Asymmetric oxidation of silyl enol ethers using chiral dioxiranes derived from α-fluoro cyclohexanones [J].

Solladié-Cavallo, A ;

Lupattelli, P ;

Jierry, L ;

Bovicelli, P ;

Angeli, F ;

Antonioletti, R ;

Klein, A .

TETRAHEDRON LETTERS, 2003, 44 (34) :6523-6526

[32] ALPHA-OXYGENATION OF A TRANS-3,4-DISUBSTITUTED GAMMA-LACTONE - A COMPARATIVE-STUDY [J].

TASCHNER, MJ ;

AMINBHAVI, AS .

TETRAHEDRON LETTERS, 1989, 30 (09) :1029-1032

[33] STUDIES DIRECTED TOWARD TAXANES - PREPARATION OF ALPHA-KETOLS BY OXIDATIVE RING-OPENING OF EPOXIDES [J].

TROST, BM ;

FRAY, MJ .

TETRAHEDRON LETTERS, 1988, 29 (18) :2163-2166

[34] Ligand-dependent reversal of facial selectivity in the asymmetric dihydroxylation [J].

Vanhessche, KPM ;

Sharpless, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7978-7979

[35]

Vedejs E., 1986, ORG SYNTH, V64, p[127, 127]

[36] NMR STUDIES ON ENOLIZATION OF 1-PARA-CHLOROPHENYL-1-HYDROXY-2-PROPANONE [J].

WARREN, RJ ;

RAVIN, LJ ;

BEGOSH, PP ;

SHAMI, EG ;

ZAREMBO, JE .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1971, 60 (05) :801-&

[37] A highly stereoselective entry to α-hydroxy carboxylic acids using D-fructose diacetonide as a chiral auxiliary [J].

Yu, HW ;

Ballard, E ;

Wang, BH .

TETRAHEDRON LETTERS, 2001, 42 (10) :1835-1838

← 1 2 3 4 →