Synthesis and use of enantiomerically pure tert-leucine

被引：183

作者：

Bommarius, AS ^{[1
]}

Schwarm, M ^{[1
]}

Stingl, K ^{[1
]}

Kottenhahn, M ^{[1
]}

Huthmacher, K ^{[1
]}

Drauz, K ^{[1
]}

机构：

[1] DEGUSSA AG, ORGAN CHEM R&D ICFE, D-63403 HANAU, GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 12期

关键词：

D O I：

10.1016/0957-4166(95)00377-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Owing to its bulky, inflexible and hydrophobic tert-butyl side chain, tert-leucine (Tle) finds increased use in templates or catalysts in asymmetric synthesis as well as in peptidic medicinal compounds. (S)-Tle, available through a large-scale enzymatic reductive amination process, has been incorporated into a variety of anti-AIDS and -cancer compounds. With two new routes to (R)-Tle coming available, the number of applications of both (R)- and (S)-Tle can be expected to increase considerably.

引用

页码：2851 / 2888

页数：38

共 189 条

[1] Investigation on the configurative behaviour of pseudolucine in the Walden inversion and on the secession of halogen through diluted alkali from stereoisomeric alpha-bromine-beta-trimethyl-propionyl-amino acids.
Abderhalden, E
Faust, W
Haase, E
[J]. HOPPE-SEYLERS ZEITSCHRIFT FUR PHYSIOLOGISCHE CHEMIE, 1934, 228 : 187 - 197
[2] ABDERHALDEN E, 1927, Z PHYSL CHEM, V163, P149
[3] AN IMPROVED, CONVENIENT PROCEDURE FOR REDUCTION OF AMINO-ACIDS TO AMINOALCOHOLS - USE OF NABH4-H2SO4
ABIKO, A
MASAMUNE, S
[J]. TETRAHEDRON LETTERS, 1992, 33 (38) : 5517 - 5518
[4] PREPARATION OF NOVEL SULFUR AND PHOSPHORUS-CONTAINING OXAZOLINES AS LIGANDS FOR ASYMMETRIC CATALYSIS
ALLEN, JV
DAWSON, GJ
FROST, CG
WILLIAMS, JMJ
COOTE, SJ
[J]. TETRAHEDRON, 1994, 50 (03) : 799 - 808
[5] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS
ALLEN, JV
COOTE, SJ
DAWSON, GJ
FROST, CG
MARTIN, CJ
WILLIAMS, JMJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2065 - 2072
[6] ANATOL J, 1972, B SOC CHIM FR, P189
[7] ANATOL J, 1971, SYNTH-INT J METHODS, P538
[8] THE ASYMMETRIC KHARASCH REACTION - CATALYTIC ENANTIOSELECTIVE ALLYLIC ACYLOXYLATION OF OLEFINS WITH CHIRAL COPPER(I) COMPLEXES AND TERT-BUTYL PERBENZOATE
ANDRUS, MB
ARGADE, AB
CHEN, X
PAMMENT, MG
[J]. TETRAHEDRON LETTERS, 1995, 36 (17) : 2945 - 2948
[9] ANELLI PL, 1987, J ORG CHEM, V52, P2559
[10] AN INHIBITOR OF THE PROTEASE BLOCKS MATURATION OF HUMAN AND SIMIAN IMMUNODEFICIENCY VIRUSES AND SPREAD OF INFECTION
ASHORN, P
MCQUADE, TJ
THAISRIVONGS, S
TOMASSELLI, AG
TARPLEY, WG
MOSS, B
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (19) : 7472 - 7476

← 1 2 3 4 5 6 7 8 9 10 →