A new route to (2S,4R)- and (2R,4S)-4-hydroxypipecolic acid

被引：26

作者：

Haddad, M ^{[1
]}

Larchevêque, M ^{[1
]}

机构：

[1] Ecole Natl Super Chim Paris, CNRS, Organ Synth Lab, F-75231 Paris 05, France

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(99)00458-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 [无机化学]; 081704 [应用化学];

摘要：

Both enantiomers of cis-4-hydroxypipecolic acid have been prepared by asymmetric synthesis using (S)- or (R)-glycidol as the chiral source, and involving a stereoselective hydrogenation of a six-membered cyclic imine. The latter is obtained by reduction and cyclization of a cyano beta-hydroxy ketone. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4231 / 4237

页数：7

共 17 条

[1]

Enantioselective synthesis of 3-deoxy-(R)-sphingomyelin from (S)-1-(4′-methoxyphenyl)glycerol [J].

Byun, HS ;

Sadlofsky, JA ;

Bittman, R .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2560-2563

[2]

A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[3]

EASY DIRECT STEREOSELECTIVE AND REGIOSELECTIVE FORMATION OF BETA-HYDROXY NITRILES BY REACTION OF 1,2-EPOXIDES WITH POTASSIUM CYANIDE IN THE PRESENCE OF METAL-SALTS [J].

CHINI, M ;

CROTTI, P ;

FAVERO, L ;

MACCHIA, F .

TETRAHEDRON LETTERS, 1991, 32 (36) :4775-4778

[4]

4-HYDROXYPIPECOLIC ACID FRM ACACIA SPECIES, AND ITS STEREOISOMERS [J].

CLARKLEWIS, J ;

MORTIMER, PI .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JAN) :189-&

[5]

Deslongchamps P., 1983, STEREOELECTRONIC EFF, P209

[6]

Enantioselective synthesis of (2R,4S)- and (2S,4R)-4-hydroxypipecolic acid from D-glucoheptono-1,4-lactone [J].

Di Nardo, C ;

Varela, O .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17) :6119-6125

[7]

TIN TETRACHLORIDE-INDUCED PI-CYCLIZATIONS OF GLYCINE CATION EQUIVALENTS TO SUBSTITUTED PIPECOLIC ACID-DERIVATIVES [J].

ESCH, PM ;

BOSKA, IM ;

HIEMSTRA, H ;

DEBOER, RF ;

SPECKAMP, WN .

TETRAHEDRON, 1991, 47 (24) :4039-4062

[8]

STEREOSPECIFIC SYNTHESIS OF THREO-GAMMA-HYDROXYHOMO-L-ARGININE FROM LATHYRUS SPECIES [J].

FUJITA, Y ;

KOLLONITSCH, J ;

WITKOP, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (09) :2030-+

[9]

Practical access to highly enantioenriched C-3 building blocks via hydrolytic kinetic resolution [J].

Furrow, ME ;

Schaus, SE ;

Jacobsen, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6776-6777

[10]

Preparation of (2S,4R)-4-hydroxypipecolic acid and derivatives [J].

Gillard, J ;

Abraham, A ;

Anderson, PC ;

Beaulieu, PL ;

Bogri, T ;

Bousquet, Y ;

Grenier, L ;

Guse, I ;

Lavallee, P .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2226-2231

← 1 2 →